Recent Advances in Ynamide Coupling Reagent

doi:10.6023/cjoc202011022

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (3): 873-887.DOI: 10.6023/cjoc202011022 Previous Articles Next Articles

Special Issue: 热点论文虚拟合集

ACCOUNT

炔酰胺类缩合剂研究进展

刘涛^a^,^b, 许泗林^c, 赵军锋^a^,^b^,^*()

a 西北工业大学化学制造研究院西安 710072
b 江西师范大学化学化工学院南昌 330022
c 许昌学院数理学院河南许昌 461000

收稿日期:2020-11-16 修回日期:2020-12-11 发布日期:2020-12-24
通讯作者: 赵军锋

作者简介:

刘涛, 2017年毕业于江西农业大学理学院, 2018年进入江西师范大学化学化工学院有机化学专业攻读硕士学位, 师从赵军锋教授. 主要从事多肽绿色合成方法研究.

许泗林, 2015年于许昌学院获得学士学位, 2015~2020年在江西师范大学赵军锋教授课题组硕博连读, 于2020年7月获得博士学位, 同年9月进入许昌学院任讲师. 主要研究方向为多肽的化学合成与修饰和新型荧光探针的设计与合成.

赵军锋, 教授, 洪堡学者. 2001年和2005年分别于北京师范大学和华中师范大学获学士和硕士学位. 2010年获新加坡南洋理工大学博士学位. 2010~2013年先后于南洋理工大学、德国波恩大学和明斯特大学从事化学生物学方向学的博士后研究; 2013~2014年任香港大学化学系助理教授(研究); 2014~2020年任江西师范大学教授、博士生导师; 2021年起,任西北工业大学教授、博士生导师. 课题组致力于通过发展有机化学新反应和新试剂来解决化学生物学的前沿科学问题, 研究兴趣集中在多肽与蛋白质的化学合成与精准修饰及其化学生物学研究.

基金资助:
国家自然科学基金(21778025); 国家自然科学基金(91853114)

Recent Advances in Ynamide Coupling Reagent

Tao Liu^a^,^b, Silin Xu^c, Junfeng Zhao^a^,^b^,^*()

a Institute of Advanced Synthesis, Northwestern Polytechnical University, Xi'an 710072
b College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022
c School of Science, Xuchang University, Xuchang, Henan 461000

Received:2020-11-16 Revised:2020-12-11 Published:2020-12-24
Contact: Junfeng Zhao
About author:
* Corresponding author. E-mail: zhaojf@jxnu.edu.cn
Supported by:
National Natural Science Foundation of China(21778025); National Natural Science Foundation of China(91853114)

Coupling or condensation reagents are compounds that can be used to promote the direct condensation of carboxylic acids with amines or alcohols to furnish amide or ester bond, respectively. Since their discovery, coupling reagents have been widely used in the manufacture of drugs, materials, cosmetics and other fine chemicals containing amide or ester bond. In particular, coupling reagent plays a crucial role in the chemical synthesis of peptides which involves the iterative amide bond formation between proteinogenic α-amino acids. However, current peptide synthesis methods and strategies are mainly relied on the reagents and techniques developed in 1950~1980s, and are reaching a high standard and their inherent limits. For example, the impurities and racemization/epmimerization caused by over activation of conventional coupling reagents have become major concerns of peptide drug manufacture. Moreover, the poor atom economy of the solid phase peptide synthesis results in large amount of chemical waste, and thus posing formidable challenge to the sustainable development. Only disruptive innovations involving new reagents and novel condensation mechanism can solve the notorious issues that plague current peptide synthesis. In this context, our research group disclosed that ynamide could be used as a novel coupling reagent to promote amide and ester bond formation via the condensation of carboxylic acids with amines or alcohols. More importantly, ynamide coupling reagents could also be used for peptide bond formation in a racemization free manner. Herein, the discovery as well as the application of ynamide coupling reagent in the construction of amide and ester bonds is systematically summarized.

Key words: ynamide, coupling reagent, amide bond, peptide synthesis, ester bond, macrolactone, thiopeptide

Cite this article

Tao Liu, Silin Xu, Junfeng Zhao. Recent Advances in Ynamide Coupling Reagent[J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 873-887.

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Fig. & Tab. 22

Scheme 1. Amide bond formation from condensation of carboxylic acid and amine

Scheme 2. Racemization mechanism during peptide bond formation

Figure 1. Representative racemization suppressors

Figure 2. Representative coupling reagents

Scheme 3. Alkyne coupling reagents mediated amide bond formation

Scheme 4. Discovery of ynamide coupling reagents

Scheme 5. Ynamide-mediated “one-pot” synthesis of aimdes

Table 1. Optimization of the ynamide

Table 2. Ynamide-mediated amide synthesis

Entry	Coupling reagent	Additive	Time	Yield^b/%	dr^c
1	HBTU	DIEA	10 min	90	82∶18
2	HATU	DIEA	10 min	70	87∶13
3	PyBop	DIEA	10 min	91	88∶12
4	DEPBT	DIEA	20 min	61	99∶1
5	DCC	—	10 min	98	91∶9
6	MYMsA	—	22 h	99	>99∶1
7	MYTsA	—	22 h	94	>99∶1

Table 3. Comparative study of racemization/epimerization of peptide bond formation

Table 4. Ynamide-mediated peptide synthesis

Scheme 6. Ynamide-mediated intermolecular esterification and macrolactonization

Table 5. Ynamide-mediated intermolecular esterification

Table 6. Ynamide-mediated macrolactonization

Entry	Reaction conditions	I I:II'^b	Yield^c/%	dr
1	DCC, DMAP, CSA, CHCl₃, r.t., 4 h	98∶2	34	89∶11
2	EDCI, HOAT, DMAP, CH- Cl₃, r.t., 4 h	69∶31	13	37∶63
3	HBTU, DMAP, CHCl₃, r.t., 2 h	90∶10	20	23∶77
4	TBTU, HOAT, DMAP, CH₂- Cl₂, r.t., 1 h	>99∶1	33	69∶31
5	HATU, DMAP, CHCl₃, r.t., 30 min	78∶22	38	93∶7
6	PyBop, DMAP, CH₂Cl₂, r.t., 2 h	46∶54	12	27∶73
7	PySSPy, PPh₃, MeCN, 80 ℃, 8 h	21∶79	5	92∶8
8	PPh₃, DEAD, THF, r.t., 48 h	>99∶1	6	29∶71
9	2-methyl-6-nitrobenzoic anhydride, DMAP, NEt₃, toluene, 25 ℃	nd	(52)	94∶6
10	MYTsA, PTSA?H₂O, CH₂- Cl₂, r.t., 10 min	>99∶1	87 (92)	>99∶1

Table 7. Comparative study of macrolactonization methods

Scheme 7. Ynamide-mediated thioamide synthesis

Table 8. Chemoselective synthesis of thioacylation reagents

Table 9. Ynamide-mediated thioamide substituted peptide synthesis

Scheme 8. Synthesis of trithioamide-substituted Leu-enkephalin

Scheme 9. Site-specific incorporation of thioamide substitution into a peptide backbone via solid phase peptide synthesis

Table 10. Ynamide-mediated thionoester and dithioester synthesis

Table 11. A robust one-step approach to ynamides

References 68

[1]	Lundberg, H.; Tinnis, F.; Selander, N.; Adolfsson, H. Chem. Soc. Rev. 2014, 43, 2714. pmid: 24430887
[2]	Roughley, S. D.; Jordan, A. M. J. Med. Chem. 2011, 54, 3451. pmid: 21504168
[3]	(a) Valeur, E.; Bradley, M. Chem. Soc. Rev. 2009, 38, 606. pmid: 21416075
	(b) Han, S. Y.; Kim, Y. A. Tetrahedron 2004, 60, 2447. pmid: 21416075
	(c) Montalbetti, C. A. G. N.; Falque, V. Tetrahedron 2005, 61, 10827. pmid: 21416075
	(d) Hackenberger, C. P.; Schwarzer, D. Angew. Chem., Int. Ed. 2008, 47, 10030. pmid: 21416075
	(e) de Figueiredo, R.M.; Suppo,, J. S.; Campagne,, J. M. Chem. Rev. 2016, 116, 12029. pmid: 21416075
	(f) Dunetz, J. R.; Magano, J.; Weisenburger, G. A. Org. Process Res. Dev. 2016, 20, 140. pmid: 21416075
	(g) El-Faham, A.; Albericio, F. Chem. Rev. 2011, 111, 6557. pmid: 21416075
	(h) Pattabiraman, V. R.; Bode, J. W. Nature 2011, 480, 471. pmid: 21416075
	(i) Allen, C. L.; Williams, J. M. Chem. Soc. Rev. 2011, 40, 3405. pmid: 21416075
[4]	(a) Zompra, A. A.; Galanis, A. S.; Werbitzky, O.; Albericio, F. Future Med. Chem. 2009, 1, 361. pmid: 28720325
	(b) Henninot, A.; Collins, J. C.; Nuss, J. M. J. Med. Chem. 2018, 61, 1382. pmid: 28720325
	(c) Lau, J. L.; Dunn, M. K. Bioorg. Med. Chem. 2018, 26, 2700. pmid: 28720325
[5]	Sheehan, J. C.; Hess, G. P. J. Am. Chem. Soc. 1955, 77, 1067.
[6]	Benoiton, N. L.; Chen, F. M. F. J. Chem. Soc.,Chem. Commun. 1981, 543.
[7]	Sheehan, J.; Cruickshank, P.; Boshart, G. J. Org. Chem. 1961, 26, 2525.
[8]	Coste, J.; Le-Nguyen, D.; Castro, B. Tetrahedron Lett. 1990, 31, 205.
[9]	Carpino, L. A.; El-Faham, A.; Albericio, F. Tetrahedron Lett. 1994, 35, 2279. doi: 10.1016/0040-4039(94)85198-0
[10]	Dourtoglou, V.; Ziegler, J.-C.; Gross, B. Tetrahedron Lett. 1978, 19, 1269.
[11]	Marder, O.; Shvo, Y.; Albericio, F. Chim. Oggi 2002, 20, 37.
[12]	(a) Wehrstedt, K. D.; Wandrey, P. A.; Heitkamp, D. J. Hazard. Mater. 2005, 126, 1. doi: 10.1016/j.jhazmat.2005.05.044 pmid: 16084016
	(b) Malow, M.; Wehrstedt, K. D.; Neuenfeld, S. Tetrahedron Lett. 2007, 48, 1233. pmid: 16084016
[13]	Subiros-Funosas, R.; Prohens, R.; Barbas, R.; El-Faham, A.; Albericio, F. Chem.-Eur. J. 2009, 15, 9394. pmid: 19575348
[14]	Sperry, J. B.; Minteer, C. J.; Tao, J. Y.; Johnson, R.; Duzguner, R.; Hawksworth, M.; Oke, S.; Richardson, P. F.; Barnhart, R.; Bill, D. R.; Giusto, R. A.; Weaver, J. D. Org. Process Res. Dev. 2018, 22, 1262. doi: 10.1021/acs.oprd.8b00193
[15]	(a) El-Faham, A.; Subiros Funosas, R.; Prohens, R.; Albericio, F. Chem.-Eur. J. 2009, 15, 9404. pmid: 19621394
	(b) Subiros-Funosas, R.; Acosta, G. A.; El-Faham, A.; Albericio, F. Tetrahedron Lett. 2009, 50, 6200. pmid: 19621394
[16]	Belleau, B.; Malek, G. J. Am. Chem. Soc. 1968, 90, 1651. pmid: 5636806
[17]	Paul, R.; Anderson, G. W. J. Am. Chem. Soc. 1960, 82, 4596.
[18]	Kaminski, Z. J.; Kolesinska, B.; Kolesinska, J.; Sabatino, G.; Chelli, M.; Rovero, P.; Blaszczyk, M.; Glowka, M. L.; Papini, A. M. J. Am. Chem. Soc. 2005, 127, 16912. pmid: 16316237
[19]	Gong, Y. T.; Du, Y. C.; Huang, W. D.; Chen, C. Q.; Ge, L. T.; Hu, J. Y.; Niu, S. Q.; Xu, J. C.; Zhang, W. J.; Chen, L. L.; Li, H. X.; Wang, Y.; Lu, D. P.; Ji, A. X.; Li, C. X.; Shi, B. T.; Ye, Y. H.; Tang, K. L.; Xing, Q. Y. Chin. Sci. Bull. 1965, 16, 941. (in Chinese)
	(龚岳亭, 杜雨苍, 黄惟德, 陈常庆, 葛麟俊, 胡世全, 蒋荣庆, 朱尚权, 钮经义, 徐杰诚, 张伟君, 陈玲玲, 李鸿绪, 汪猷, 陆德培, 季爱雪, 李崇熙, 施溥涛, 叶蕴华, 汤卡罗, 邢其毅, 科学通报, 1965, 16, 941.)
[20]	(a) Li, P.; Xu, J. C. Tetrahedron Lett. 1999, 40, 3605. pmid: 11532072
	(b) Li, P.; Xu, J. C. Tetrahedron 2000, 56, 4437. pmid: 11532072
	(c) Li, P.; Xu, J. C. J. Pept. Res. 2001, 58, 129. doi: 10.1034/j.1399-3011.2001.00867.x pmid: 11532072
[21]	Hamuro, Y.; Scialdone, M. A.; DeGrado, W. F. J. Am. Chem. Soc. 1999, 121, 1636.
[22]	(a) Zheng, J. S.; Tang, S.; Huang, Y. C.; Liu, L. Acc. Chem. Res. 2013, 46, 2475. doi: 10.1021/ar400012w pmid: 28374993
	(b) Fang, G. M.; Li, Y. M.; Shen, F.; Huang, Y. C.; Li, J. B.; Lin, Y.; Cui, H. K.; Liu, L. Angew. Chem., Int. Ed. 2011, 50, 7645. doi: 10.1002/anie.201100996 pmid: 28374993
	(c) Fang, G.-M.; Wang, J.-X.; Liu, L. Angew. Chem., Int. Ed. 2012, 51, 10347. pmid: 28374993
	(d) Li, J. B.; Tang, S.; Zheng, J. S.; Tian, C. L.; Liu, L. Acc. Chem. Res. 2017, 50, 1143. pmid: 28374993
	(e) Zhang, B.; Deng, Q.; Zuo, C.; Yan, B.; Zuo, C.; Cao, X. X.; Zhu, T. F.; Zheng, J. S.; Liu, L. Angew. Chem., Int. Ed. 2019, 58, 12231. pmid: 28374993
[23]	(a) Zhang, Y.; Xu, C.; Lam, H. Y.; Lee, C. L.; Li, X. Proc. Natl. Acad. Sci. U. S. A. 2013, 110, 6657. pmid: 29979577
	(b) Li, X.; Lam, H. Y.; Zhang, Y.; Chan, C. K. Org. Lett. 2010, 12, 1724. doi: 10.1021/ol1003109 pmid: 29979577
	(c) Wong, C. T. T.; Lam, H. Y.; Song, T.; Chen, G.; Li, X. Angew. Chem., Int. Ed. 2013, 52, 10212. pmid: 29979577
	(d) Lee, C. L.; Liu, H.; Wong, C. T. T.; Chow, H. Y.; Li, X. J. Am. Chem. Soc. 2016, 138, 10477. doi: 10.1021/jacs.6b04238 pmid: 29979577
	(e) Liu, H.; Li, X. Acc. Chem. Res. 2018, 51, 1643. pmid: 29979577
[24]	(a) Cai, H.; Chen, M.-S.; Sun, Z.-Y.; Zhao, Y.-F.; Kunz, H.; Li, Y.-M. Angew. Chem. Int. Ed. 2013, 52, 6106. pmid: 28448716
	(b) Cai, H.; Sun, Z. Y.; Chen, M. S.; Zhao, Y. F.; Kunz, H.; Li, Y. M. Angew. Chem., Int. Ed. 2014, 53, 1699. pmid: 28448716
	(c) Huang, Z. H.; Shi, L.; Ma, J. W.; Sun, Z. Y.; Cai, H.; Chen, Y. X.; Zhao, Y. F.; Li, Y. M. J. Am. Chem. Soc. 2012, 134, 8730. doi: 10.1021/ja211725s pmid: 28448716
	(d) He, Y. H.; Li, Y. M.; Chen, Y. X. Talanta 2016, 150, 340. pmid: 28448716
	(e) Zhang, S. Y.; Sperlich, B.; Li, F. Y.; Al-Ayoubi, S.; Chen, H. X.; Zhao, Y. F.; Li, Y. M.; Weise, K.; Winter, R.; Chen, Y. X. ACS Chem. Biol. 2017, 12, 1703. pmid: 28448716
[25]	(a) Gui, Y.; Qiu, L.; Li, Y.; Li, H.; Dong, S. J. Am. Chem. Soc. 2016, 138, 4890. doi: 10.1021/jacs.6b01202 pmid: 32787248
	(b) Chen, X.; Ye, F.; Luo, X.; Liu, X.; Zhao, J.; Wang, S.; Zhou, Q.; Chen, G.; Wang, P. J. Am. Chem. Soc. 2019, 141, 18230. pmid: 32787248
	(c) Zhang, X.; Lu, G.; Sun, M.; Mahankali, M.; Ma, Y.; Zhang, M.; Hua, W.; Hu, Y.; Wang, Q.; Chen, J.; He, G.; Qi, X.; Shen, W.; Liu, P.; Chen, G. Nat. Chem. 2018, 10, 540. doi: 10.1038/s41557-018-0006-y pmid: 32787248
	(d) Li, B.; Li, X.; Han, B.; Chen, Z.; Zhang, X.; He, G.; Chen, G. J. Am. Chem. Soc. 2019, 141, 9401. pmid: 32787248
	(e) Lu, S.; Wu, Y.; Li, J.; Meng, X.; Hu, C.; Zhao, Y.; Wu, C. J. Am. Chem. Soc. 2020, 142, 16285. pmid: 32787248
	(f) Yin, Y.; Fei, Q.; Liu, W.; Li, Z.; Suga, H.; Wu, C. Angew. Chem., Int. Ed. 2019, 58, 4880. pmid: 32787248
	(g) Zheng, Y.; Meng, X.; Wu, Y.; Zhao, Y.; Wu, C. Chem. Sci. 2018, 9, 569. doi: 10.1039/c7sc03956e pmid: 32787248
	(h) Zhan, B. B.; Li, Y.; Xu, J. W.; Nie, X. L.; Fan, J.; Jin, L.; Shi, B. F. Angew. Chem., Int. Ed. 2018, 57, 5858. pmid: 32787248
	(i) Zhan, B.-B.; Fan, J.; Jin, L.; Shi, B.-F. ACS Catal. 2019, 9, 3298. pmid: 32787248
	(j) Wang, C.; Guo, M.; Qi, R.; Shang, Q.; Liu, Q.; Wang, S.; Zhao, L.; Wang, R.; Xu, Z. Angew. Chem., Int. Ed. 2018, 57, 15841. pmid: 32787248
	(k) Wang, C.; Qi, R.; Xue, H.; Shen, Y.; Chang, M.; Chen, Y.; Wang, R.; Xu, Z. Angew. Chem., Int. Ed. 2020, 59, 7461. pmid: 32787248
	(l) Bai, Z.; Cai, C.; Yu, Z.; Wang, H. Angew. Chem., Int. Ed. 2018, 57, 13912. pmid: 32787248
	(m) Tang, J.; Chen, H.; He, Y.; Sheng, W.; Bai, Q.; Wang, H. Nat. Commun. 2018, 9, 3383. pmid: 32787248
	(n) Yin, H.; Zheng, M.; Chen, H.; Wang, S.; Zhou, Q.; Zhang, Q.; Wang, P. J. Am. Chem. Soc. 2020, 142, 14201. pmid: 32787248
	(o) Wang, C.; Guo, M.; Qi, R.; Shang, Q.; Liu, Q.; Wang, S.; Zhao, L.; Wang, R.; Xu, Z., Angew. Chem., Int. Ed. 2018, 57, 15841. doi: 10.1002/anie.201809400 pmid: 32787248
	(p) Wang, C.; Qi, R.; Xue, H.; Shen, Y.; Chang, M.; Chen, Y.; Wang, R.; Xu, Z. Angew. Chem., Int. Ed. 2020, 59, 7461. pmid: 32787248
[26]	(a) Li, H.; Chao, J.; Hasan, J.; Tian, G.; Jin, Y.; Zhang, Z.; Qin, C. J. Org. Chem. 2020, 85, 6271. pmid: 32275447
	(b) Li, H. D.; Chao, J.; Tian, G.; Hasan, J.; Jin, Y. T.; Zhang, Z. X.; Qin, C. G. Org. Chem. Front. 2020, 7, 689. pmid: 32275447
	(c) Li, H.; Chao, J.; Zhang, Z.; Tian, G.; Li, J.; Chang, N.; Qin, C. Org. Lett. 2020, 22, 3323. pmid: 32275447
[27]	(a) Tian, J.; Gao, W.-C.; Zhou, D.-M.; Zhang, C. Org. Lett. 2012, 14, 3020. pmid: 26252539
	(b) Zhang, C.; Liu, S.-S.; Sun, B.; Tian, J. Org. Lett. 2015, 17, 4106. pmid: 26252539
[28]	(a) Zhang, B.; Li, Y.; Shi, W.; Wang, T.; Zhang, F.; Liu, L. Chem. Res. Chin. Univ. 2020, 36, 733. pmid: 31050890
	(b) Dawson, P.; Muir, T.; Clark-Lewis, I.; Kent, S. Science 1994, 266, 776. pmid: 31050890
	(c) Kent, S. B. Chem. Soc. Rev. 2009, 38, 338. pmid: 31050890
	(d) Jin, K.; Li, X. Chem.-Eur. J. 2018, 24, 17397. doi: 10.1002/chem.201802067 pmid: 31050890
	(e) Zheng, J.-S.; Tang, S.; Huang, Y.-C.; Liu, L. Acc. Chem. Res. 2013, 46, 2475. pmid: 31050890
	(f) Rohde, H.; Seitz, O. Biopolymers 2010, 94, 551. doi: 10.1002/bip.21442 pmid: 31050890
	(g) Yang, R.; Pasunooti, K. K.; Li, F.; Liu, X. W.; Liu, C. F. J. Am. Chem. Soc. 2009, 131, 13592. doi: 10.1021/ja905491p pmid: 31050890
	(h) Agouridas, V.; El Mahdi, O.; Diemer, V.; Cargoët, M.; Monbaliu, J.-C. M.; Melnyk, O. Chem. Rev. 2019, 119, 7328. doi: 10.1021/acs.chemrev.8b00712 pmid: 31050890
	(i) Yang, J.; Zhao, J. Sci. China: Chem. 2018, 61, 97. pmid: 31050890
[29]	Merrifield, R. B. J. Am. Chem. Soc. 1963, 85, 2149.
[30]	(a) Coin, I.; Beyermann, M.; Bienert, M. Nat. Protoc. 2007, 2, 3247. pmid: 24559202
	(b) Zheng, J.-S.; Yu, M.; Qi, Y.-K.; Tang, S.; Shen, F.; Wang, Z.-P.; Xiao, L.; Zhang, L.; Tian, C.-L.; Liu, L. J. Am. Chem. Soc. 2014, 136, 3695. pmid: 24559202
[31]	Constable, D. J. C.; Dunn, P. J.; Hayler, J. D.; Humphrey, G. R.; Leazer, J. J. L.; Linderman, R. J.; Lorenz, K.; Manley, J.; Pearlman, B. A.; Wells, A.; Zaks, A.; Zhang, T. Y. Green Chem. 2007, 9, 411.
[32]	(a) Wang, T.; Yuan, L.; Zhao, Z. G.; Shao, A. L.; Gao, M.; Huang, Y. F.; Xiong, F.; Zhang, H. L.; Zhao, J. F. Green Chem. 2015, 17, 2741. doi: 10.1039/C5GC00299K
	(b) Zhao, Z. G.; Wang, T.; Yuan, L.; Hu, X.; Xiong, F.; Zhao, J. F. Adv. Synth. Catal. 2015, 357, 2566.
	(c) Zhao, Z. G.; Wang, T.; Yuan, L.; Jia, X. W.; Zhao, J. F. RSC Adv. 2015, 5, 75386. doi: 10.1039/C5RA16658F
[33]	Arens, J. F. Recl. Trav. Chim. Pays-Bas 1955, 74, 769.
[34]	(a) Kita, Y.; Akai, S.; Ajimura, N.; Yoshigi, M.; Tsugoshi, T.; Yasuda, H.; Tamura, Y. J. Org. Chem. 1986, 51, 4150. pmid: 27282773
	(b) Krause, T.; Baader, S.; Erb, B.; Goossen, L. J. Nat. Commun. 2016, 7, 11732. doi: 10.1038/ncomms11732 pmid: 27282773
	(c) Wasserman, H. H.; Wharton, P. S. Tetrahedron 1958, 3, 321. pmid: 27282773
	(d) Kita, Y.; Maeda, H.; Omori, K.; Okuno, T.; Tamura, Y. Synlett 1993,273. pmid: 27282773
	(e) Wasserman, H. H.; Wharton, P. S. J. Am. Chem. Soc. 1960, 82, 661. pmid: 27282773
[35]	Buijle, R.; Viehe, H. G. Angew. Chem., Int. Ed. 1964, 3, 582.
[36]	Gais, H.-J. Angew. Chem., Int. Ed. 1978, 17, 597.
[37]	Lienhard, U.; Fahrni, H.-P.; Neuenschwander, M. Helv. Chim. Acta. 1978, 61, 1609. doi: 10.1002/(ISSN)1522-2675
[38]	Viehe, H. G.; van Vyve, T.; Janousek, Z. Angew. Chem., Int. Ed. 1972, 11, 916.
[39]	(a) Huang, B.; Zeng, L.; Shen, Y.; Cui, S. Angew. Chem., Int. Ed. 2017, 56, 4565. pmid: 33651602
	(b) Zeng, L.; Lin, Y.; Li, J.; Sajiki, H.; Xie, H.; Cui, S. Nat. Commun. 2020, 11, 5639. pmid: 33651602
	Zeng, L.; Cui, S. Chin. J. Org. Chem. 2020, 40, 2353. (in Chinese) doi: 10.6023/cjoc202003045 pmid: 33651602
	(曾林伟, 崔孙良, 有机化学, 2020, 40, 2353.) pmid: 33651602
	(d) Shu, C.; Wang, Y. H.; Zhou, B.; Li, X. L.; Ping, Y. F.; Lu, X.; Ye, L. W. J. Am. Chem. Soc. 2015, 137, 9567. doi: 10.1021/jacs.5b06015 pmid: 33651602
	(e) Hong, F. L.; Chen, Y. B.; Ye, S. H.; Zhu, G. Y.; Zhu, X. Q.; Lu, X.; Liu, R. S.; Ye, L. W. J. Am. Chem. Soc. 2020, 142, 7618. doi: 10.1021/jacs.0c01918 pmid: 33651602
	(f) Hong, F. L.; Ye, L. W. Acc. Chem. Res. 2020, 53, 2003. doi: 10.1021/acs.accounts.0c00417 pmid: 33651602
	(g) Wang, Z. S.; Chen, Y. B.; Zhang, H. W.; Sun, Z.; Zhu, C.; Ye, L. W. J. Am. Chem. Soc. 2020, 142, 3636. pmid: 33651602
	(h) Ye, L. W.; Zhu, X. Q.; Sahani, R. L.; Xu, Y.; Qian, P. C.; Liu, R. S. Chem. Rev. 2020, DOI: 10.1021/acs.chemrev.0c00348. doi: 10.1021/acs.chemrev.0c01055 pmid: 33651602
[40]	(a) Evano, G.; Coste, A.; Jouvin, K. Angew. Chem., Int. Ed. 2010, 49, 2840. pmid: 33135691
	(b) DeKorver, K. A.; Li, H.; Lohse, A. G.; Hayashi, R.; Lu, Z.; Zhang, Y.; Hsung, R. P. Chem. Rev. 2010, 110, 5064. doi: 10.1021/cr100003s pmid: 33135691
	(c) Chen, Y. B.; Qian, P. C.; Ye, L. W. Chem. Soc. Rev. 2020, 49, 8897. doi: 10.1039/d0cs00474j pmid: 33135691
[41]	Smith, D. L.; Goundry, W. R.; Lam, H. W. Chem. Commun. 2012, 48, 1505.
[42]	Xu, S.; Liu, J.; Hu, D.; Bi, X. Green Chem. 2015, 17, 184.
[43]	Hu, L.; Xu, S.; Zhao, Z.; Yang, Y.; Peng, Z.; Yang, M.; Wang, C.; Zhao, J. J. Am. Chem. Soc. 2016, 138, 13135. pmid: 27685176
[44]	Chang, H. N.; Liu, B. Y.; Qi, Y. K.; Zhou, Y.; Chen, Y. P.; Pan, K. M.; Li, W. W.; Zhou, X. M.; Ma, W. W.; Fu, C. Y.; Qi, Y. M.; Liu, L.; Gao, Y. F. Angew. Chem., Int. Ed. 2015, 54, 11760.
[45]	(a) Neises, B.; Steglich, W. Angew. Chem., Int. Ed. 1978, 17, 522. doi: 10.1002/(ISSN)1521-3773 pmid: 11073448
	(b) Fischer, E.; Speier, A. Ber. Dtsch. Chem. Ges. 1895, 28, 3252. pmid: 11073448
	(c) Tu, Y.; Yuan, L.; Wang, T.; Wang, C.; Ke, J.; Zhao, J. J. Org. Chem. 2017, 82, 4970. doi: 10.1021/acs.joc.7b00499 pmid: 11073448
	(d) De, Sarkar, S.; Grimme,, S.; Studer,, A. J. Am. Chem. Soc. 2010, 132, 1190. pmid: 11073448
	(e) Ogawa, H.; Chihara, T.; Taya, K. J. Am. Chem. Soc. 1985, 107, 1365. pmid: 11073448
	(f) Xu, T.; Alper, H. J. Am. Chem. Soc. 2014, 136, 16970. pmid: 11073448
	(g) Ishihara, K.; Ohara, S.; Yamamoto, H. Science 2000, 290, 1140. pmid: 11073448
[46]	Wang, X.; Yang, Y.; Zhao, Y.; Wang, S.; Hu, W.; Li, J.; Wang, Z.; Yang, F.; Zhao, J. J. Org. Chem. 2020, 85, 6188. doi: 10.1021/acs.joc.0c00485 pmid: 32227863
[47]	Parenty, A.; Moreau, X.; Niel, G.; Campagne, J. M. Chem. Rev. 2013, 113, PR1. pmid: 23005342
[48]	Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989.
[49]	(a) Furstner, A.; Bouchez, L. C.; Funel, J. A.; Liepins, V.; Poree, F. H.; Gilmour, R.; Beaufils, F.; Laurich, D.; Tamiya, M. Angew. Chem., Int. Ed. 2007, 46, 9265. doi: 10.1002/(ISSN)1521-3773
	(b) Furstner, A.; Aissa, C.; Chevrier, C.; Teply, F.; Nevado, C.; Tremblay, M. Angew. Chem., Int. Ed. 2006, 45, 5832.
	(c) Zhuo, C. X.; Furstner, A. Angew. Chem., Int. Ed. 2016, 55, 6051.
[50]	Yang, M.; Wang, X. W.; Zhao, J. F. ACS Catal. 2020, 10, 5230.
[51]	Cochrane, J. R.; Yoon, D. H.; McErlean, C. S.; Jolliffe, K. A. Beilstein J. Org. Chem. 2012, 8, 1344. doi: 10.3762/bjoc.8.154 pmid: 23019469
[52]	(a) Mahanta, N.; Szantai-Kis, D. M.; Petersson, E. J.; Mitchell, D. A. ACS Chem. Biol. 2019, 14, 142. pmid: 29064683
	(b) Müller, M. M. Biochemistry 2018, 57, 177. doi: 10.1021/acs.biochem.7b00861 pmid: 29064683
[53]	(a) Clausen, K.; Spatola, A. F.; Lemieux, C.; Schiller, P. W.; Lawesson, S. O. Biochem. Biophys. Res. Commun. 1984, 120, 305. pmid: 9871586
	(b) Seebach, D.; Ko, S. Y.; Kessler, H.; Köck, M.; Reggelin, M.; Schmieder, P.; Walkinshaw, M. D.; Bölsterli, J. J.; Bevec, D. Helv. Chim. Acta 1991, 74, 1953. pmid: 9871586
	(c) Yao, S.; Zutshi, R.; Chmielewski, J. Bioorg. Med. Chem. Lett. 1998, 8, 699. doi: 10.1016/s0960-894x(98)00100-0 pmid: 9871586
[54]	Szantai-Kis, D.; Walters, C.; Barrett, T.; Hoang, E.; Petersson, E. Synlett 2017, 28, 1789.
[55]	Kato, S.; Akada, W.; Mizuta, M.; Ishii, Y. Bull. Chem. Soc. Jpn. 1973, 46, 244.
[56]	(a) Hoeeg-Jensen, T.; Olsen, C. E.; Holm, A. J. Org. Chem. 1994, 59, 1257.
	(b) Høeg-Jensen, T.; Havsteen Jakobsen, M.; Olsen, C. E.; Holm, A. Tetrahedron Lett. 1991, 32, 7617.
[57]	Yang, J.; Wang, C.; Xu, S.; Zhao, J. Angew. Chem., Int. Ed. 2019, 58, 1382.
[58]	Mukherjee, S.; Verma, H.; Chatterjee, J. Org. Lett. 2015, 17, 3150. pmid: 26061484
[59]	Yang, J.; Wang, C.; Yao, C.; Chen, C.; Hu, Y.; He, G.; Zhao, J. J. Org. Chem. 2020, 85, 1484. pmid: 31789513
[60]	Jones, B. A.; Bradshaw, J. S. Chem. Rev. 1984, 84, 17.
[61]	(a) Cerda, M. M.; Newton, T. D.; Zhao, Y.; Collins, B. K.; Hendon, C. H.; Pluth, M. D. Chem. Sci. 2019, 10, 1773. pmid: 30230325
	(b) Cerda, M. M.; Zhao, Y.; Pluth, M. D. J. Am. Chem. Soc. 2018, 140, 12574. pmid: 30230325
[62]	Yao, C.; Yang, J.; Lu, X.; Zhang, S.; Zhao, J. Org. Lett. 2020, 22, 6628. pmid: 32806151
[63]	Evano, G.; Blanchard, N.; Compain, G.; Coste, A.; Demmer, C. S.; Gati, W.; Guissart, C.; Heimburger, J.; Henry, N.; Jouvin, K.; Karthikeyan, G.; Laouiti, A.; Lecomte, M.; Martin-Mingot, A.; Metayer, B.; Michelet, B.; Nitelet, A.; Theunissen, C.; Thibaudeau, S.; Wang, J. J.; Zarca, M.; Zhang, C. Y. Chem. Lett. 2016, 45, 574. doi: 10.1246/cl.160260
[64]	Hamada, T.; Ye, X.; Stahl, S. S. J. Am. Chem. Soc. 2008, 130, 833. pmid: 18166058
[65]	(a) Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1998, 37, 489.
	(b) Rainier, J. D.; Imbriglio, J. E. Org. Lett. 1999, 1, 2037.
	(c) Witulski, B.; Lumtscher, J.; Bergstrasser, U. Synlett 2003,708.
[66]	Coste, A.; Karthikeyan, G.; Couty, F.; Evano, G. Angew. Chem., Int. Ed. 2009, 48, 4381.
[67]	(a) Tu, Y.; Zeng, X.; Wang, H.; Zhao, J. Org. Lett. 2018, 20, 280. pmid: 30843394
	(b) Zeng, X.; Tu, Y.; Zhang, Z.; You, C.; Wu, J.; Ye, Z.; Zhao, J. J. Org. Chem. 2019, 84, 4458. doi: 10.1021/acs.joc.8b03192 pmid: 30843394
[68]	Song, Q.; Kong, L.; Zhu, L.; Hong, R.; Huang, S. H. Chin. J. Chem. 2020, 39, 1022.

炔酰胺类缩合剂研究进展

Recent Advances in Ynamide Coupling Reagent

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