Synthesis and Application of Organic Hypervalent Bromine Reagents

doi:10.6023/A23040173

Acta Chimica Sinica ›› 2023, Vol. 81 ›› Issue (8): 1030-1042.DOI: 10.6023/A23040173 Previous Articles Next Articles

Review

有机高价溴试剂的合成及其应用研究

甘绍艳, 钟晟昱, 王力廷, 史雷^*()

哈尔滨工业大学(深圳)理学院深圳 518055

投稿日期:2023-04-30 发布日期:2023-09-14

作者简介:

甘绍艳, 1990年出生于河南省濮阳市, 2013年本科毕业于郑州大学药学院, 2022年博士毕业于哈尔滨工业大学化工与化学学院, 主要从事基于有机过氧化物氧化策略的含杂原子化合物的合成研究.

钟晟昱, 1998年出生于安徽省合肥市, 2019年在淮北师范大学获得学士学位. 现为哈尔滨工业大学(深圳)理学院化学工程与技术专业博士研究生, 主要研究课题为高价卤素试剂促进的不对称反应.

王力廷, 于2021年在哈尔滨工业大学取得硕士学位, 并于2021年加入哈尔滨工业大学(深圳)史雷教授的课题组, 现为哈尔滨工业大学(深圳)理学院化学工程与技术专业博士二年级研究生, 主要从事金属催化的不对称反应工作.

史雷, 哈尔滨工业大学(深圳)理学院教授、博士生导师.于2000年本科毕业于兰州大学, 2005年博士毕业于兰州大学. 先后在德国亚琛工业大学、德国慕尼黑大学以及英国牛津大学从事博士后研究. 2011年加入哈尔滨工业大学开展独立研究工作, 目前研究兴趣集中在基于氧化/还原策略的新试剂、新反应及机理研究以及基于重要优势骨架的不对称催化合成研究.

基金资助:
项目受国家自然科学基金(22271069); 项目受国家自然科学基金(21871067); 广东省基础与应用基础研究基金项目(2021A1515010190); 广东省基础与应用基础研究基金项目(2023A1515012457)

Synthesis and Application of Organic Hypervalent Bromine Reagents

Shaoyan Gan, Shengyu Zhong, Liting Wang, Lei Shi()

School of Science, Harbin Institute of Technology (Shenzhen), Shenzhen 518055

Received:2023-04-30 Published:2023-09-14
Contact: *E-mail: lshi@hit.edu.cn
Supported by:
National Natural Science Foundation of China(22271069); National Natural Science Foundation of China(21871067); Guangdong Basic and Applied Basic Research Foundation(2021A1515010190); Guangdong Basic and Applied Basic Research Foundation(2023A1515012457)

In recent decades, with the rapid development of organic synthetic chemistry, organic hypervalent halogen reagents have drawn considerable research interest on the synthesis and application of organic hypervalent bromine reagents. Compared with traditional organic hypervalent iodine reagents, organic hypervalent bromine reagents have stronger oxidation capacity and reactivity, thus enabling their important application potential in organic synthesis. On the basis of different substituents of organic hypervalent bromine reagents, the diaryl-λ³-bromanes, dialkyl-λ³-bromanes, alkenyl-λ³-bromanes, alkyne-λ³-bromanes and heteroatomic-λ³-bromanes are summarized and discussed successively. The synthetic methods of different types of hypervalent bromine reagents and their applications in organic reactions are also reviewed.

Key words: organic hypervalent bromine reagent, organic synthesis, synthetic application, synthetic method, reaction type

Cite this article

Shaoyan Gan, Shengyu Zhong, Liting Wang, Lei Shi. Synthesis and Application of Organic Hypervalent Bromine Reagents[J]. Acta Chimica Sinica, 2023, 81(8): 1030-1042.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 23

Figure 1. Hypervalent molecules

Figure 2. Synthesis and reactivity of hypervalent iodines and bromines

Figure 3. Synthesis of diaryl-λ3-bromanes

Figure 4. Cyclic diaryl-λ3-bromanes serving as aryne precursors in the construction of C—O and C—N bonds

Figure 5. A rapid access to molecular complexity via cycloaddition reactions

Figure 6. Diaryl-λ3-bromanes catalyzed Michael addition of indole to α,β-unsaturated ketones

Figure 7. Application of chiral cyclic diaryl-λ3-bromanes (III) based on binaphthalene structure in Vinylogous Mannich reaction

Figure 8. Synthesis of dialkyl-λ3-bromanes

Figure 9. Synthesis of alkenyl-λ3-bromanes

Figure 10. Synthesis and solvolysis of cyclic vinyl-λ3-bromanes

Figure 11. Synthesis and application of (E)-β-alkylvinyl(aryl)-λ3-bromanes

Figure 12. Synthesis and application of alkynyl-λ3-bromanes

Figure 13. Synthesis of symmetrical 1,3-butadiynes

Figure 14. Reaction of alkynyl-λ3-bromanes with 2-mercapto-1,3-benzazoles

Figure 15. Reaction of phenylsulfonylimino-λ3-bromanes with olefins

Figure 16. C—H amination of unactivated hydrocarbons and its mechanism

Figure 17. Reaction of phenylsulfonylimino-λ3-bromanes with N-heterocycles and trialkylamines

Figure 18. Difluoro-λ3-bromanes-induced oxidative carbon-carbon bond-forming reactions

Figure 19. Difluoro-λ3-bromanes strategy for Baeyer-Villiger oxidation

Figure 20. Research of bis(perfluoroalkanesulfonyl)bromonium ylides

Figure 21. Synthesis of heteroxy cyclic-λ3-bromane

Figure 22. Electrochemical synthesis of cyclic-λ3-bromanes and its application

Figure 23. Synthesis and reactivities of air- and moisture-stable λ3?bromanes

References 49

[1]	Musher J. I. Angew. Chem., Int. Ed. 1969, 8, 54. doi: 10.1002/(ISSN)1521-3773
[2]	Jensen W. B. J. Chem. Educ. 2006, 83, 1751. doi: 10.1021/ed083p1751
[3]	Pauling L. J. Am. Chem. Soc. 1932, 54, 3570. doi: 10.1021/ja01348a011
[4]	Zhu D.; Yao Y.; Zhao R.; Liu Y.; Shi L. Chem.-Eur. J. 2018, 24, 4805. doi: 10.1002/chem.201800555
[5]	Taylor M. T.; Nelson J. E.; Suero M. G.; Gaunt M. J. Nature 2018, 562, 563. doi: 10.1038/s41586-018-0608-y
[6]	Banik S. M.; Medley J. W.; Jacobsen E. N. Science 2016, 353, 6294.
[7]	(a) Yoshimura A.; Zhdankin V. V. Chem. Rev. 2016, 116, 3328. doi: 10.1021/acs.chemrev.5b00547
	(b) Zhao R.; Shi L. Angew. Chem., Int. Ed. 2020, 59, 12282. doi: 10.1002/anie.v59.30
	(c) Zhdankin V. V.; Stang P. J. Chem. Rev. 2008, 108, 5299. doi: 10.1021/cr800332c
	(d) Song A. R.; Zhang C. Acta Chim. Sinica 2015, 73, 1002. (in Chinese)
	( 宋爱茹, 张弛, 化学学报, 2015, 73, 1002.)
	(e) Duan Y. N.; Jiang S. N.; Han Y. C.; Sun B.; Zhang C. Chin. J. Org. Chem. 2016, 36, 1973. (in Chinese) doi: 10.6023/cjoc201605007
	( 段亚南, 姜山, 韩永超, 孙博, 张弛, 有机化学, 2016, 36, 1973.)
	(f) Cai Q.; Ma H. W. Acta Chim. Sinica 2019, 77, 213. (in Chinese) doi: 10.6023/A18110470
	( 蔡倩, 马浩文, 化学学报, 2019, 77, 213.)
[8]	Pauling L. J. Am. Chem. Soc. 1932, 54, 3570. doi: 10.1021/ja01348a011
[9]	CRC Handbook of Chemistry and Physics, Ed.: Lide, D. R., CRC Press, Boca Raton, FL, 1992, pp. 1-2408.
[10]	(a) Ochiai M. Synlett 2009, 159.
	(b) Farooq U.; Shah A.-H. A.; Wirth T. Angew. Chem., Int. Ed. 2009, 48, 101. doi: 10.1002/(ISSN)1521-3757
	(c) Miyamoto K. PATAI’S Chemistry of Functional Groups, Ed.: Rappoport, Z., Wiley, Chichester, 2018, pp. 1-25.
[11]	Leneau P. Ann. Chim. Phys. 1906, 9, 241.
[12]	Sandin R. B.; Hay A. S. J. Am. Chem. Soc. 1952, 74, 274.
[13]	Miyamoto K.; Saito M.; Tsuji S.; Takagi T.; Shiro M.; Uchiyama M.; Ochiai M. J. Am. Chem. Soc. 2021, 143, 9327. doi: 10.1021/jacs.1c04536
[14]	(a) Nesmeyanov A. N.; Vanchikov A. N.; Lisichkina I. N.; Lazarev V. V.; Tolstaya T. P. Dokl. Akad. Nauk SSSR 1980, 255, 1136.
	(b) Nesmeyanov A. N.; Vanchikov A. N.; Lisichkina I. N.; Khruscheva N. S.; Tolstaya T. P. Dokl. Akad. Nauk SSSR 1980, 254, 652.
[15]	Holleman A. F.; Wiberg E. Inorganic Chemistry, Academic Press, San Diego, 2001.
[16]	Frohn H. J.; Giesen M. J. Fluorine Chem. 1984, 24, 9. doi: 10.1016/S0022-1139(00)81292-0
[17]	Lanzi M.; Dherbassy Q.; Wencel-Delord J. Angew. Chem., Int. Ed. 2021, 60, 14852. doi: 10.1002/anie.v60.27
[18]	(a) Grushin V. V. Chem. Soc. Rev. 2000, 29, 315. doi: 10.1039/a909041j
	(b) Chatterjee N.; Goswami A. Eur. J. Org. Chem. 2017, 2017, 3023. doi: 10.1002/ejoc.v2017.21
[19]	Lanzi M.; Ali Abdine R. A.; De Abreu M.; Wencel-Delord J. Org. Lett. 2021, 23, 9047. doi: 10.1021/acs.orglett.1c03278
[20]	Zhang Y.; Han J.; Liu Z. RSC Adv. 2015, 5, 25485. doi: 10.1039/C5RA00209E
[21]	Yoshida Y.; Ishikawa S.; Mino T.; Sakamoto M. Chem. Commun. 2021, 57, 2519. doi: 10.1039/D0CC07733J
[22]	Yoshida Y.; Mino T.; Sakamoto M. ACS Catal. 2021, 11, 13028. doi: 10.1021/acscatal.1c04070
[23]	Olah G. A.; DeMember J. R. J. Am. Chem. Soc. 1969, 91, 2113. doi: 10.1021/ja01036a044
[24]	Slebocka-Tilk H.; Ball R. G.; Brown R. S. J. Am. Chem. Soc. 1985, 107, 4504. doi: 10.1021/ja00301a021
[25]	Prakash G. K. S.; Bruce M. R.; Olah G. A. J. Org. Chem. 1985, 50, 2405. doi: 10.1021/jo00213a050
[26]	Ochiai M.; Nishi Y.; Mori T.; Tada N.; Suefuji T.; Frohn H. J. J. Am. Chem. Soc. 2005, 127, 10460. doi: 10.1021/ja051690f
[27]	Miyamoto K.; Shiro M.; Ochiai M. Angew. Chem., Int. Ed. 2009, 48, 8931. doi: 10.1002/anie.200903368
[28]	Ochiai M. J. Organomet. Chem. 2000, 611, 494. doi: 10.1016/S0022-328X(00)00487-3
[29]	Ochiai M.; Okubo T.; Miyamoto K. J. Am. Chem. Soc. 2011, 133, 3342. doi: 10.1021/ja200479p
[30]	Ochiai M.; Tada N.; Okada T.; Sota A.; Miyamoto K. J. Am. Chem. Soc. 2008, 130, 2118. doi: 10.1021/ja074624h
[31]	Ochiai M.; Nishi Y.; Goto S.; Shiro M.; Frohn H. J. J. Am. Chem. Soc. 2003, 125, 15304. doi: 10.1021/ja038777q
[32]	(a) Kitamura T.; Stang P. J. J. Org. Chem. 1988, 53, 4105. doi: 10.1021/jo00252a042
	(b) Stang P.J.; Surber B. W.; Chen Z.-C.; Roberts K. A.; Anderson A. G. J. Am. Chem. Soc. 1987, 109, 228. doi: 10.1021/ja00235a034
[33]	Ochiai M.; Nishi Y.; Goto S.; Shiro M.; Frohn H. J. J. Am. Chem. Soc. 2003, 125, 15304. doi: 10.1021/ja038777q
[34]	(a) Donaldson R. E.; Fuchs P. L. J. Am. Chem. Soc. 1981, 103, 2108. doi: 10.1021/ja00398a048
	(b) Saddler J. C.; Fuchs P. L. J. Am. Chem. Soc. 1981, 103, 2112. doi: 10.1021/ja00398a050
	(c) Paquette L. A.; Lin H. S.; Gunn B. P.; Coghlan M. J. J. Am. Chem. Soc. 1988, 110, 5818. doi: 10.1021/ja00225a037
[35]	Ochiai M.; Nishi Y.; Goto S.; Frohn H. J. Angew. Chem., Int. Ed. 2005, 44, 406.
[36]	Ochiai M.; Tada N. Chem. Commun. 2005, 5083.
[37]	(a) Evans D. A.; Faul M. M.; Bilodeau M. T. J. Am. Chem. Soc. 1994, 116, 2742. doi: 10.1021/ja00086a007
	(b) Li Z.; Quan R. W.; Jacobsen E. N. J. Am. Chem. Soc. 1995, 117, 5889. doi: 10.1021/ja00126a044
[38]	Ochiai M.; Kaneaki T.; Tada N.; Miyamoto K.; Chuman H.; Shiro M.; Hayashi S.; Nakanishi W. J. Am. Chem. Soc. 2007, 129, 12938. doi: 10.1021/ja075811i
[39]	Hoque M. M.; Miyamoto K.; Tada N.; Shiro M.; Ochiai M. Org. Lett. 2011, 13, 5428. doi: 10.1021/ol201868n
[40]	Miyamoto K.; Ota T.; Hoque M. M.; Ochiai M. Org. Biomol. Chem. 2015, 13, 2129. doi: 10.1039/C4OB02160F
[41]	Espino C. G.; Bois J. D. In Modern Rhodium-Catalyzed Organic Reactions, Ed.: Evans, P. A., Wiley-VCH, Weinheim, 2005, p. 379 and references therein.
[42]	Ochiai M.; Miyamoto K.; Kaneaki T.; Hayashi S.; Nakanishi W.; Science 2011, 332, 448. doi: 10.1126/science.1201686
[43]	Miyamoto K.; Shiro M.; Ochiai M. Angew. Chem., Int. Ed. 2009, 48, 8931. doi: 10.1002/anie.200903368
[44]	Ochiai M.; Yoshimura A.; Mori T.; Nishi Y.; Hirobe M. J. Am. Chem. Soc. 2008, 130, 3742. doi: 10.1021/ja801097c
[45]	Ochiai M.; Yoshimura A.; Miyamoto K.; Hayashi S.; Nakanishi W. J. Am. Chem. Soc. 2010, 132, 9236. doi: 10.1021/ja104330g
[46]	Ochiai M.; Tada N.; Murai K.; Goto S.; Shiro M. J. Am. Chem. Soc. 2006, 128, 9608. doi: 10.1021/ja063492+
[47]	Miyamoto K.; Iwasaki S.; Doi R.; Ota T.; Kawano Y.; Yamashita J.; Sakai Y.; Tada N.; Ochiai M.; Hayashi S.; Nakanishi W.; Uchiyama M. J. Org. Chem. 2016, 81, 3188. doi: 10.1021/acs.joc.6b00142
[48]	Nguyen T. T.; Martin J. C. J. Am. Chem. Soc. 1980, 102, 7382. doi: 10.1021/ja00544a047
[49]	Sokolovs I.; Mohebbati N.; Francke R.; Suna E. Angew. Chem., Int. Ed. 2021, 60, 15832.

有机高价溴试剂的合成及其应用研究

Synthesis and Application of Organic Hypervalent Bromine Reagents

RichHTML

PDF

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 23

References 49

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Yandong Zhang, Shoufei Zhu. Perspective for Phosphine Ligands with Cyclopropane Backbone^★ [J]. Acta Chimica Sinica, 2023, 81(7): 777-783.
[2]	Li Liu, Gang Zheng, Guoqiang Fan, Hongguang Du, Jiajing Tan. Research Progress in Organic Reactions Involving 4-Acyl/Carbamoyl/Alkoxycarbonyl Substituted Hantzsch Esters [J]. Acta Chimica Sinica, 2023, 81(6): 657-668.
[3]	Qi Xueping, Wang Fei, Zhang Jian. A Post-Synthetic Method for the Construction of Titanium-Based Metal Organic Frameworks and Their Applications [J]. Acta Chimica Sinica, 2023, 81(5): 548-558.
[4]	Ying Wei, Ping Zhou, Xin Chen, Qiujing Bao, Linghai Xie. Research Progress on Organic Nanohoops/Nanogrids [J]. Acta Chimica Sinica, 2023, 81(3): 289-308.
[5]	Xia Liu, Chunxiang Kuang, Changhui Su. Transition-metal Catalyzed 1,2,3-Triazole-assisted C—H Functionalization Processes [J]. Acta Chimica Sinica, 2022, 80(8): 1135-1151.
[6]	Wei Zheyu, Chang Yalin, Yu Han, Han Sheng, Wei Yongge. Application of Anderson Type Heteropoly Acids as Catalysts in Organic Synthesis [J]. Acta Chimica Sinica, 2020, 78(8): 725-732.
[7]	Huang Pei-Qiang. Direct Transformations of Amides: Tactics and Recent Progress [J]. Acta Chim. Sinica, 2018, 76(5): 357-365.
[8]	Li Shu-Sen, Wang Jianbo. Recent Advance in Asymmetric Trifluoromethylthiolation [J]. Acta Chim. Sinica, 2018, 76(12): 913-924.
[9]	Du Jin, Lin Ning, Qian Yitai. Recent Development of the Synthetic Method for Si/Graphite Anode Materials [J]. Acta Chimica Sinica, 2017, 75(2): 147-153.
[10]	Qiu Di, Qiu Menglong, Ma Rong, Zhang Yan, Wang Jianbo. Nitrogen Group Retaining Reaction in the Transformation of Diazo Compounds [J]. Acta Chim. Sinica, 2016, 74(6): 472-487.
[11]	Liu Rong, Feng Jing, Liu Bo. Synthetic Progress of Daphnane-type Diterpenoids [J]. Acta Chim. Sinica, 2016, 74(1): 24-43.
[12]	XIONG Yun; LIU Qing-Yao; LI Zi-Fu; WANG Hong; YANG Ya-Jiang*. Reaction-type Gelators of Dialkylurea Derivatives and the Gelation of Organic Solvents at Room Temperature [J]. Acta Chimica Sinica, 2008, 66(3): 391-397.
[13]	LIU Yong-Jun, ZHANG Yong-Min*. New Progress in the Application of Samarium Reagent to Organic Synthesis [J]. Acta Chimica Sinica, 2005, 63(5): 341-351.
[14]	CHEN JIANXIN;PAN JIGANG;XIA CHIZHONG;CHENG JINPEI. Mimicking of structure and properties of tetrahydrofolic coenzyme and study on their substituted one-carbon unit transfer reactions [J]. Acta Chimica Sinica, 1998, 56(8): 819-826.
[15]	GAO XIANG;ZENG JIN;ZHOU JINGYAO;WU SHIHUI. Samarium in organic synthesis.Ⅱ.reaction of allyl halides with esters in the presence of samarium metal [J]. Acta Chimica Sinica, 1993, 51(12): 1191-1194.