Site-Selective C—H Iodination of Phenol Derivatives Using Aryl Iodide as Iodinating Reagent

doi:10.6023/cjoc202106011

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (9): 3511-3520.DOI: 10.6023/cjoc202106011 Previous Articles Next Articles

Special Issue: 热点论文虚拟合集

ARTICLES

以芳基碘为碘化试剂的苯酚衍生物的位点选择性C—H键碘化反应

张涛^a, 李尚达^b^,^*(), 周春林^b, 王新超^b, 张孟^b, 高泽众^b, 李纲^b^,^*()

a 中北大学理学院山西太原 030051
b 中国科学院福建物质结构研究所煤制乙二醇及相关技术重点实验室福州 350002

收稿日期:2021-06-06 修回日期:2021-06-07 发布日期:2021-06-07
通讯作者: 李尚达, 李纲
基金资助:
国家自然科学基金(22022111); 国家自然科学基金(22071248); 福建省自然科学基金(2020J02008); 福建省自然科学基金(2020J01108); 中国科学院青年创新促进会(2020306)

Site-Selective C—H Iodination of Phenol Derivatives Using Aryl Iodide as Iodinating Reagent

Tao Zhang^a, Shangda Li^b(), Chunlin Zhou^b, Xinchao Wang^b, Meng Zhang^b, Zezhong Gao^b, Gang Li^b()

a School of Science, North University of China, Taiyuan, Shanxi 030051
b Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002

Received:2021-06-06 Revised:2021-06-07 Published:2021-06-07
Contact: Shangda Li, Gang Li
Supported by:
National Natural Science Foundation of China(22022111); National Natural Science Foundation of China(22071248); Natural Science Foundation of Fujian Province(2020J02008); Natural Science Foundation of Fujian Province(2020J01108); Youth Innovation Promotion Association of the Chinese Academy of Sciences(2020306)

1. .pdf(5590KB)

Abstract

Site-selective C—H iodination of electron-rich phenols is a challenging reaction. A Pd(II)-catalyzed C—H iodination of free 2-aryl phenols and 2-phenoxyacetic acids using 4-iodo-3-nitroanisole as the mild iodinating reagent was reported. Excellent site-selectivity and good functional group tolerance were obtained with a range of electron rich phenol derivatives. These results suggest that C—H iodination via formal metathesis is a potentially useful method for C—H iodination of challenging substrates.

Key words: C—H iodination, formal metathesis, site-selectivity, phenol, aryl iodide, palladium catalysis

Cite this article

Tao Zhang, Shangda Li, Chunlin Zhou, Xinchao Wang, Meng Zhang, Zezhong Gao, Gang Li. Site-Selective C—H Iodination of Phenol Derivatives Using Aryl Iodide as Iodinating Reagent[J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3511-3520.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 5

References 16

[1]	(a) Bringmann, G.; Gulder, T.; Gulder, T. A.; Breuning, M. Chem. Rev. 2011, 111, 563. doi: 10.1021/cr100155e pmid: 20939606
	(b) Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359. doi: 10.1021/cr000664r pmid: 20939606
	(c) Qin, L.; Ren, L.; Wan, S.; Liu, G.; Luo, X.; Liu, Z.; Li, F.; Yu, Y.; Liu, J.; Wei, Y. J. Med. Chem. 2017, 60, 3606. doi: 10.1021/acs.jmedchem.7b00254 pmid: 20939606
[2]	Reed, M. A.; Chang, M. T.; Snieckus, V. Org. Lett. 2004, 6, 2297. doi: 10.1021/ol049740t
[3]	(a) Liao, G.; Shi, B. Acta Chim. Sinica 2015, 73, 1283. (in Chinese). doi: 10.6023/A15040295 pmid: 27341176
	( 廖港, 史炳锋, 化学学报, 2015, 73, 1283.) pmid: 27341176
	(b) Petrone, D. A.; Ye, J.; Lautens, M. Chem. Rev. 2016, 116, 8003. doi: 10.1021/acs.chemrev.6b00089 pmid: 27341176
	(c) Luo, J.; Xu, X.; Zhao, Y.; Liang, H. Chin. J. Org. Chem. 2017, 37, 2873. (in Chinese). doi: 10.6023/cjoc201705018 pmid: 27341176
	( 骆钧飞, 徐星, 赵延超, 梁洪泽, 有机化学, 2017, 37, 2873.) pmid: 27341176
	(d) Das, R.; Kapur, M. Asian J. Org. Chem. 2018, 7, 1524. doi: 10.1002/ajoc.201800142 pmid: 27341176
[4]	(a) Giri, R.; Chen, X.; Yu, J. Q. Angew. Chem., nt. Ed. 2005, 44, 2112. pmid: 22548632
	(b) Wan, X.; Ma, Z.; Li, B.; Zhang, K.; Cao, S.; Zhang, S.; Shi, Z. J. Am. Chem. Soc. 2006, 128, 7416. doi: 10.1021/ja060232j pmid: 22548632
	(c) Kalyani, D.; Dick, A. R.; Anani, W. Q.; Sanford, M. S. Org. Lett. 2006, 8, 2523. doi: 10.1021/ol060747f pmid: 22548632
	(d) Mei, T.-S.; Giri, R.; Maugel, N.; Yu, J.-Q. Angew. Chem., nt. Ed. 2008, 47, 5215. pmid: 22548632
	(e) Schröder, N.; Wencel-Delord, J.; Glorius, F. J. Am. Chem. Soc. 2012, 134, 8298. doi: 10.1021/ja302631j pmid: 22548632
	(f) Wang, X.-C.; Hu, Y.; Bonacorsi, S.; Hong, Y.; Burrell, R.; Yu, J.-Q. J. Am. Chem. Soc. 2013, 135, 10326. doi: 10.1021/ja4055492 pmid: 22548632
	(g) Urones, B.; Martínez, Á. M.; Rodríguez, N.; Arrayás, R. G.; Carretero, J. C. Chem. Commun. 2013, 49, 11044. doi: 10.1039/c3cc47174h pmid: 22548632
	(h) Chu, L.; Xiao, K.-J.; Yu, J.-Q. Science 2014, 346, 451. pmid: 22548632
	(i) Gao, D.-W.; Gu, Q.; You, S.-L. ACS Catal. 2014, 4, 2741. doi: 10.1021/cs500813z pmid: 22548632
	(j) Lu, C.; Zhang, S.-Y.; He, G.; Nack, W. A.; Chen, G. Tetrahedron 2014, 70, 4197. doi: 10.1016/j.tet.2014.02.070 pmid: 22548632
	(k) Aihara, Y.; Chatani, N. ACS Catal. 2016, 6, 4323. doi: 10.1021/acscatal.6b00964 pmid: 22548632
	(l) Zhan, B.-B.; Liu, Y.-H.; Hu, F.; Shi, B.-F. Chem. Commun. 2016, 52, 4934. doi: 10.1039/C6CC00822D pmid: 22548632
	(i) Fan, X.-M.; Guo, Y.; Li, Y.-D.; Yu, K.-K.; Liu, H.-W.; Liao, D.-H.; Ji, Y.-F. Asian J. Org. Chem. 2016, 5, 499. doi: 10.1002/ajoc.v5.4 pmid: 22548632
	(m) Li, J.; Cong, W.; Gao, Z.; Zhang, J.; Yang, H.; Jiang, G. Org. Biomol. Chem. 2018, 16, 3479. doi: 10.1039/C8OB00318A pmid: 22548632
	(n) Schreib, B. S.; Carreira, E. M. J. Am. Chem. Soc. 2019, 141, 8758. doi: 10.1021/jacs.9b03998 pmid: 22548632
[5]	Sun, X.; Yao, X.; Zhang, C.; Rao, Y. Chem. Commun. 2015, 51, 10014. doi: 10.1039/C5CC02533H
[6]	(a) Youn, S. W.; Cho, C. G. Org. Biomol. Chem. 2021, DOI: 10. 1039/d1ob00506e.
	(b) Xu, X.; Luo, J. ChemSusChem 2019, 12, 4601. doi: 10.1002/cssc.v12.20
[7]	(a) Bedford, R. B.; Engelhart, J. U.; Haddow, M. F.; Mitchell, C. J.; Webster, R. L. Dalton Trans. 2010, 39, 10464. doi: 10.1039/c0dt00385a pmid: 20931130
	(b) John, A.; Nicholas, K. M. J. Org. Chem. 2012, 77, 5600. doi: 10.1021/jo300713h pmid: 20931130
	(c) Sun, X.; Sun, Y.; Zhang, C.; Rao, Y. Chem. Commun. 2014, 50, 1262. doi: 10.1039/C3CC47431C pmid: 20931130
[8]	(a) Bhawal, B. N.; Morandi, B. Angew. Chem., nt. Ed. 2019, 58, 10074. pmid: 31283206
	(b) Yu, B.; Zou, S.; Liu, H.; Huang, H. J. Am. Chem. Soc. 2020, 142, 18341. doi: 10.1021/jacs.0c10615 pmid: 31283206
	(c) Yu, B.; Zou, S.; Huang, H. J. Org. Chem. 2021, 86, 7849. doi: 10.1021/acs.joc.1c00752 pmid: 31283206
	(d) Rochette, E.; Desrosiers, V.; Soltani, Y.; Fontaine, F. G. J. Am. Chem. Soc. 2019, 141, 12305. doi: 10.1021/jacs.9b04305 pmid: 31283206
	(e) Baba, K.; Tobisu, M.; Chatani, N. Angew. Chem., nt. Ed. 2013, 52, 11892. pmid: 31283206
	(f) Shao, Y.; Zhang, F.; Zhang, J.; Zhou, X. Angew. Chem., nt. Ed. 2016, 55, 11485. pmid: 31283206
	(g) Fan, C.; Lv, X.-Y.; Xiao, L.-J.; Xie, J.-H.; Zhou, Q.-L. J. Am. Chem. Soc. 2019, 141, 2889. doi: 10.1021/jacs.8b13251 pmid: 31283206
[9]	Li, S.; Zhang, C.; Fu, L.; Wang, H.; Cai, L.; Chen, X.; Wang, X.; Li, G. CCS Chem. 2021, DOI: 10.31635/ccschem.021.202101156.
[10]	(a) Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew. Chem., nt. Ed. 1997, 36, 1740. pmid: 24620903
	(b) Xiao, B.; Gong, T.-J.; Liu, Z.-J.; Liu, J.-H.; Luo, D.-F.; Xu, J.; Liu, L. J. Am. Chem. Soc. 2011, 133, 9250. doi: 10.1021/ja203335u pmid: 24620903
	(c) Luo, S.; Luo, F.-X.; Zhang, X.-S.; Shi, Z.-J. Angew. Chem., nt. Ed. 2013, 52, 10598. pmid: 24620903
	(d) Inamoto, K.; Kadokawa, J.; Kondo, Y. Org. Lett. 2013, 15, 3962. doi: 10.1021/ol401734m pmid: 24620903
	(e) Zhang, C.; Ji, J.; Sun, P. J. Org. Chem. 2014, 79, 3200. doi: 10.1021/jo4028825 pmid: 24620903
	(f) Duan, S.; Xu, Y.; Zhang, X.; Fan, X. Chem. Commun. 2016, 52, 10529. doi: 10.1039/C6CC04756D pmid: 24620903
	(g) Fu, L.; Li, S.; Cai, Z.; Ding, Y.; Guo, X.-Q.; Zhou, L.-P.; Yuan, D.; Sun, Q.-F.; Li, G. Nat. Catal. 2018, 1, 469. doi: 10.1038/s41929-018-0080-y pmid: 24620903
	(h) Kumar, D. R.; Gopi Krishna Reddy, A.; Satyanarayana, G. Eur. J. Org. Chem. 2019, 2019, 2472. doi: 10.1002/ejoc.201801637 pmid: 24620903
[11]	(a) Wei, Y.; Yoshikai, N. Org. Lett. 2011, 13, 5504. doi: 10.1021/ol202229w pmid: 21950683
	(b) Schmidt, B.; Riemer, M. J. Heterocycl. Chem. 2017, 54, 1287. pmid: 21950683
[12]	(a) Sun, W.-W.; Cao, P.; Mei, R.-Q.; Li, Y.; Ma, Y.-L.; Wu, B. Org. Lett. 2014, 16, 480. doi: 10.1021/ol403364k
	(b) Tong, H.-R.; Zheng, W.; Lv, X.; He, G.; Liu, P.; Chen, G. ACS Catal. 2020, 10, 114. doi: 10.1021/acscatal.9b04768
	(c) Zhou, T.; Jiang, M.-X.; Yang, X.; Yue, Q.; Han, Y.-Q.; Ding, Y.; Shi, B.-F. Chin. J. Chem. 2020, 38, 242. doi: 10.1002/cjoc.v38.3
[13]	Wang, P.; Verma, P.; Xia, G.; Shi, J.; Qiao, J. X.; Tao, S.; Cheng, P. T. W.; Poss, M. A.; Farmer, M. E.; Yeung, K.-S.; Yu, J.-Q. Nature 2017, 551, 489. doi: 10.1038/nature24632
[14]	(a) Whitfield, S. R.; Sanford, M. S. J. Am. Chem. Soc. 2007, 129, 15142. pmid: 18004863
	(b) Xu, L.-M.; Li, B.-J.; Yang, Z.; Shi, Z.-J. Chem. Soc. Rev. 2010, 39, 712. doi: 10.1039/B809912J pmid: 18004863
	(c) Hickman, A. J.; Sanford, M. S. Nature 2012, 484, 177. doi: 10.1038/nature11008 pmid: 18004863
	(d) Powers, D. C.; Ritter, T. Acc. Chem. Res. 2012, 45, 840. doi: 10.1021/ar2001974 pmid: 18004863
[15]	(a) Xiao, Y.; Xu, Y.; Cheon, H.; Chae, J. J. Org. Chem. 2013, 78, 5804. doi: 10.1021/jo400702z pmid: 23713792
	(b) He, X.; Yu, Z.; Jiang, S.; Zhang, P.; Shang, Z.; Lou, Y.; Wu, J. Bioorg. Med. Chem. 2015, 25, 5601. doi: 10.1016/j.bmcl.2015.10.041 pmid: 23713792
	(c) Okaecwe, T.; Swanepoel, A.; Petzer, A.; Bergh, J.; Petzer, J. Bioorg. Med. Chem. 2012, 20, 4336. doi: 10.1016/j.bmc.2012.05.048 pmid: 23713792
[16]	Dudnik, A. S.; Chernyak, N.; Huang, C.; Gevorgyan, V. Angew. Chem., n. Ed. 2010, 49, 8729.

Entry	Ligand	Base (equiv.)	Ag salt (equiv.)	T/℃	Yield/% 2a/3a	Entry	Ligand	Base (equiv.)	Ag salt (equiv.)	T/℃	Yield/% 2a/3a
1	L1	NaOAc (0.5)	—	90	23/10	12	L3	K₂CO₃ (1.0)	AgNO₃ (0.1)	90	50/7
2	L2	NaOAc (0.5)	—	90	47/8	13	L3	K₂CO₃ (1.0)	AgBr (0.1)	90	65/6
3	L3	NaOAc (0.5)	—	90	52/10	14	L3	K₂CO₃ (1.0)	AgCl (0.2)	90	80/8
4	L3	NaOAc (1.0)	—	90	57/9	15	L3	K₂CO₃ (1.0)	AgCl (0.5)	90	66/8
5	L3	Na₂CO₃ (1.0)	—	90	73/10	16	L3	K₂CO₃ (1.0)	AgCl (0.1)	80	82/8
6	L3	K₂CO₃ (1.0)	—	90	77/7	17	L3	K₂CO₃ (1.0)	AgCl (0.1)	60	81/8
7	L3	K₂CO₃ (2.0)	—	90	72/10	18^b	L3	K₂CO₃ (1.0)	AgCl (0.1)	60	80/8
8	L3	KOH (1.0)	—	90	69/6	19^c	L3	K₂CO₃ (1.0)	AgCl (0.1)	60	82/7
9	L3	K₂CO₃ (1.0)	AgCl (0.1)	90	82/8	20^d	L2	K₂CO₃ (1.0)	AgCl (0.1)	60	25/1
10	L3	K₂CO₃ (1.0)	AgOAc (0.1)	90	50/5	21^e	L3	K₂CO₃ (1.0)	AgCl (0.1)	60	85/7^f
11	L2	K₂CO₃ (1.0)	Ag₂CO₃ (0.1)	90	63/7	22^g	L3	K₂CO₃ (1.0)	AgCl (0.1)	60	65/5

Entry	Ligand	Base (equiv.)	Ag salt (equiv.)	T/℃	Yield/% 2a/3a	Entry	Ligand	Base (equiv.)	Ag salt (equiv.)	T/℃	Yield/% 2a/3a
1	L1	NaOAc (0.5)	—	90	23/10	12	L3	K₂CO₃ (1.0)	AgNO₃ (0.1)	90	50/7
2	L2	NaOAc (0.5)	—	90	47/8	13	L3	K₂CO₃ (1.0)	AgBr (0.1)	90	65/6
3	L3	NaOAc (0.5)	—	90	52/10	14	L3	K₂CO₃ (1.0)	AgCl (0.2)	90	80/8
4	L3	NaOAc (1.0)	—	90	57/9	15	L3	K₂CO₃ (1.0)	AgCl (0.5)	90	66/8
5	L3	Na₂CO₃ (1.0)	—	90	73/10	16	L3	K₂CO₃ (1.0)	AgCl (0.1)	80	82/8
6	L3	K₂CO₃ (1.0)	—	90	77/7	17	L3	K₂CO₃ (1.0)	AgCl (0.1)	60	81/8
7	L3	K₂CO₃ (2.0)	—	90	72/10	18^b	L3	K₂CO₃ (1.0)	AgCl (0.1)	60	80/8
8	L3	KOH (1.0)	—	90	69/6	19^c	L3	K₂CO₃ (1.0)	AgCl (0.1)	60	82/7
9	L3	K₂CO₃ (1.0)	AgCl (0.1)	90	82/8	20^d	L2	K₂CO₃ (1.0)	AgCl (0.1)	60	25/1
10	L3	K₂CO₃ (1.0)	AgOAc (0.1)	90	50/5	21^e	L3	K₂CO₃ (1.0)	AgCl (0.1)	60	85/7^f
11	L2	K₂CO₃ (1.0)	Ag₂CO₃ (0.1)	90	63/7	22^g	L3	K₂CO₃ (1.0)	AgCl (0.1)	60	65/5

以芳基碘为碘化试剂的苯酚衍生物的位点选择性C—H键碘化反应

Site-Selective C—H Iodination of Phenol Derivatives Using Aryl Iodide as Iodinating Reagent

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 5

References 16

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Jingrui Wang, Yongkui Feng, Nengzhong Wang, Nianyu Huang, Hui Yao. Pd-Catalyzed Stereoselective Synthesis of Nitroalkyl β-C-Glycosides [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3216-3225.
[2]	Lu Liu, Shuguang Zhang, Renwei Hu, Xiaoxiao Zhao, Jingnan Cui, Weitao Gong. Synthesis and Properties of Phenolic Resin Polymers Based on Pillar[5]arene [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2808-2814.
[3]	Yuchao Wang, Jinbiao Liu, Zhitao He. Palladium-Catalyzed Asymmetric Hydrofunctionalizations of Conjugated Dienes [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2614-2627.
[4]	Suzhen Zhang, Wenwen Zhang, Hui Yang, Qing Gu, Shuli You. Rhodium-Catalyzed Enantioselective Spiroannulation of 2-Alkenylphenols with Alkynes [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2926-2933.
[5]	Xiaojing Hu, Feixiang Guo, Runqing Zhu, Bingqi Zhou, Tao Zhang, Lizhen Fang. Synthesis of p-Alkoxy Phenol and Its Application after Dearomatization [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2239-2244.
[6]	Jiawei Huang, Xiaoman Li, Liang Xu, Yu Wei. Electrochemical Decarboxylation Coupling of α-Keto Acids with Thiophenols: A New Avenue for the Synthesis of Thioesters [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 756-762.
[7]	Wei Xiong, Bin Shi, Xuan Jiang, Liangqiu Lu, Wenjing Xiao. Ligand-Switched Pd-Catalyzed Divergent Transformations of Vinyl Cyclic Carbamates and Isocyanates [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 265-273.
[8]	Ze Guo, Di Wu, Lili Wang, Zheng Duan. BF₃•Et₂O Promoted Dienone-Phenol Type Rearrangement to Synthesize Phosphepine with Aggregation Induced Luminescence (AIE) Effect [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2481-2487.
[9]	Tingshu Cao, Xiangyang Wei, Min Luo, Yifei Wang, Zijun Pan, Cheng Xu, Guodong Yin. PhI(OAc)₂-Promoted Dehydrogenation Oxidation for the Synthesis of 2-(Aryl/alkylthio)phenols and 10H-Phenothiazines [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2079-2088.
[10]	JIan Xiao, Zhiying Wu, Ziyi Chen, Pengfei Zhao. Tetraethylenepentamine Functionalized Phenolic Resin as Highly Active Acid-Base Bifunctional Catalyst for Knoevenagel Condensation Reaction [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1179-1187.
[11]	Hong-Chao Chen, Yichen Wu, Yang Yu, Peng Wang. Pd-Catalyzed Isomerization of Alkenes [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 742-757.
[12]	Xintuo Yang, Pinhong Chen, Guosheng Liu. Asymmetric Palladium-Catalyzed Aza-Wacker Reaction of Alkenes: Efficient Synthesis of Chiral 1,3-Oxazinan-2-ones [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3382-3389.
[13]	Shihu Jia, Siyuan Chen, Zeshui Liu, Honggang Cheng, Qianghui Zhou. Pd/Novel Axially Chiral Phosphine-Alkene Ligands Catalyzed Asymmetric Allylic Alkylation of Indoles [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3373-3381.
[14]	Jieming Zhang, Hang Ni, Qi Wu, Junfeng Yang, Junliang Zhang. Development of P, S and Si-Stereogenic Compounds Synthesis via Palladium Catalysis [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3118-3128.
[15]	Zheng Zhang, Chengqiu Dai, Honghong Wu, Jingya Li, Fajun Nan. Design and Synthesis of Alkyl Phenols Inhibitors of Death Associated Apoptotic Protein Kinase 2 (DRAK2) [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3204-3213.