C―H官能化构建硫醚

doi:10.3866/PKU.WHXB201810044

物理化学学报 >> 2019, Vol. 35 >> Issue (9): 954-967.doi: 10.3866/PKU.WHXB201810044

所属专题：碳氢键活化

C―H官能化构建硫醚

陈世豪¹,王明¹,姜雪峰^1,^2,*()

¹ 华东师范大学化学与分子工程学院，上海市绿色化学与化工过程绿色化重点实验室，上海 200062
² 中国科学院上海有机化学研究所，金属有机化学国家重点实验室，上海 200032

收稿日期:2018-10-22 录用日期:2018-11-26 发布日期:2018-11-29
通讯作者: 姜雪峰 E-mail:xfjiang@chem.ecnu.edu.cn
作者简介:姜雪峰，2003年获西北大学学士学位，2008年于中国科学院上海有机研究所获博士学位。现任华东师范大学教授、博导、教育部“青年长江学者”。研究方向为有机硫化学和方法学导向的天然产物全合成
基金资助:
国家重点研发计划(2017YFD0200500);国家自然科学基金(21722202);国家自然科学基金(21672069);国家自然科学基金(21472050);国家自然科学基金(21502054);上海市基础研究领域项目(18JC1415600);中组部“万人计划”青年拔尖人才资助

C―H Functionalization Strategies for the Construction of Thioethers

Shihao CHEN¹,Ming WANG¹,Xuefeng JIANG^1,^2,*()

¹ Shanghai Key Laboratory of Green Chemistry and Chemical Process, School of Chemistry and Molecular Engineering
² East China Normal University, Shanghai 200062, P. R. China

Received:2018-10-22 Accepted:2018-11-26 Published:2018-11-29
Contact: Xuefeng JIANG E-mail:xfjiang@chem.ecnu.edu.cn
Supported by:
the National Key Research and Development Program of China(2017YFD0200500);National Natural Science Foundation of China(21722202);National Natural Science Foundation of China(21672069);National Natural Science Foundation of China(21472050);National Natural Science Foundation of China(21502054);S&TCSM of Shanghai, China(18JC1415600);National Program for Support of Top-notch Young Professionals, China

摘要/Abstract

摘要：

硫醚作为一类重要的含硫功能分子，广泛存在于天然产物、药物及有机发光材料中。鉴于硫醚类化合物的重要性，近年来化学家们发展了一系列高效构建硫醚的方法。与传统的有机卤化物/有机硼酸与硫醇交叉偶联的合成方法相比，C―H官能化直接构建硫醚的策略因其步骤经济性、原子经济性备受合成化学家们关注，并取得重要进展。本文根据不同过渡金属进行分类，系统阐述了近年来过渡金属催化/参与C―H官能化或无过渡金属催化C―H官能化构建硫醚这一方向研究进展。

关键词: 硫醚, C―H官能化, 过渡金属, 无过渡金属催化, 含硫化合物

Abstract:

Thioesters, which are essential sulfur-containing organic molecules, are indispensable in natural products, pharmaceuticals, and organic light-emitting materials. Efficient synthesis of thioethers has received considerable attention due to the widespread applications of these compounds, and many fundamental approaches for C―S bond formation have been proposed. However, most of them construct C―S bonds by employing organic halides/organic boronic acid. These methodologies generally suffer from a pre-functionalized starting material. Recently, selective C―H functionalization emerged as a powerful tool for the synthesis of C―N, C―O, C―C, and C-halogen bonds. Nevertheless, C―S bond formation via C―H functionalization has only recently been given more importance because organosulfur compounds are believed to inactivate catalysts. In contrast to traditional cross-coupling reactions, direct functionalization of C―H bonds for the synthesis of thioethers can shorten the reaction steps and minimize the amount of waste formed. In this review, which is divided into several parts, we describe C―H functionalization strategies for the construction of thioethers. In Part Ⅰ, we introduce the importance and widespread applications of thioethers in daily life. For example, Lissoclibadin 6 is a polysulfur aromatic alkaloid that shows antimicrobial activity. Seroquel is an antipsychotic medicine. It is used to treat bipolar disorder and schizophrenia in adults, and children who are at least 10 years old. Tazarotene is approved for the treatment of psoriasis, acne, and sun-damaged skin. Furthermore, a comparison between conventional synthesis methods and C―H thiolation is discussed. In Part Ⅱ, we introduce copper-catalyzed or copper-mediated C―H thiolation. Along with the direct functionalization of sp² and sp C―H for the synthesis of aryl sulfides, some significant and challenging thiolations of sp³ C―H are included. In addition to copper, palladium is an excellent catalyst for C―H functionalization. In Part Ⅲ, we elucidate palladium-catalyzed C―H thiolation and discuss many proposed mechanisms. Nickel, which is a first-flow, low-cost, and earth-abundant metal catalyst, has increasingly gained attention. In contrast to copper and palladium, despite its late start, several remarkable reports on nickel-catalyzed C―H thiolation were published by several groups. Rhodium plays a key role in selective C―H functionalization. Some published results proved the capacity of rhodium catalysts to promote C―S construction via C―H functionalization. In Part Ⅳ, we introduce rhodium-catalyzed C―H thiolation. In recent years, metal-free C―H functionalization has been quite attractive. In Part Ⅴ, some C―S construction strategies via metal-free C―H functionalization are presented. In the last part, the conclusion discusses the limitations and possible development directions of these advances in the construction of thioethers.

Key words: Thioethers, C―H functionalization, Transition metal, Transition metal-free catalysis, Sulfur-containing compounds

MSC2000:

O643

陈世豪,王明,姜雪峰. C―H官能化构建硫醚[J]. 物理化学学报, 2019, 35(9): 954-967.

Shihao CHEN,Ming WANG,Xuefeng JIANG. C―H Functionalization Strategies for the Construction of Thioethers[J]. Acta Physico-Chimica Sinica, 2019, 35(9): 954-967.

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参考文献 130

1	Ilardi E. A. ; Vitaku E. ; Njardarson J. T. J. Med. Chem. 2014, 57, 2832. doi: 10.1021/jm401375q
2	Smith B. R. ; Eastman C. M. ; Njardarson J. T. J. Med. Chem. 2014, 57, 9764. doi: 10.1021/jm501105n
3	Feng M. ; Tang B. ; Liang S. ; Jiang X. Curr. Top. Med. Chem. 2016, 16, 1200. doi: 10.2174/1568026615666150915111741
4	Xiong H.-Y. ; Pannecoucke X. ; Besset T. Chem. -Eur. J. 2016, 22, 16734. doi: 10.1002/chem.201603438
5	Mishra A. ; Ma C. Q. ; Bäuerle P. Chem. Rev. 2009, 109, 1141. doi: 10.1021/cr8004229
6	Wang M. ; Fan Q. ; Jiang X. Org. Lett. 2016, 18, 5756. doi: 10.1021/acs.orglett.6b03078
7	Borthwick A. D. Chem. Rev. 2012, 112, 3641. doi: 10.1021/cr200398y
8	Nicolaou K. C. ; Hale C. R. H. ; Nilewski C. ; Ioannidou H. A. Chem. Soc. Rev. 2012, 41, 5185. doi: 10.1039/C2CS35116A
9	Davison E. K. ; Sperry J. J. Nat. Prod. 2017, 80, 3060. doi: 10.1021/acs.jnatprod.7b00575
10	Liu H. ; Jiang X. Chem. Asian J. 2013, 8, 2546. doi: 10.1002/asia.201300636
11	Nair D. P. ; Podgorski M. ; Shunsuke C. ; Gong T. ; Xi W. X. ; Fenoli C. R. ; Bowman C. N. Chem. Mater. 2014, 26, 724. doi: 10.1021/cm402180t
12	Bürchstümmer H. ; Weissenstein A. ; Bilalas. D. ; Würthner. F. J. Org. Chem. 2011, 76, 2426. doi: 10.1021/jo2003117
13	Takimiya K. ; Osaka I. ; Mori T. ; Nakano M. Acc. Chem. Res. 2014, 47, 1493. doi: 10.1021/ar400282g
14	Nakazawa T. ; Xu J. ; Nishikawa T. ; Oda T. ; Fujita A. ; Ukai K. ; Mangindaan R. E. P. ; Rotinsulu H. ; Kobayashi H. ; Namikoshi M. J. Nat. Prod. 2007, 70, 439. doi: 10.1021/np060593c
15	Oda T. ; Fujiwara T. ; Liu H. ; Ukai K. ; Mangindaan R. E. P. ; Mochizuki M. ; Namikoshi M. Marine Drugs 2006, 4, 15. doi: 10.3390/md401015
16	Thase M. E. ; Macfadden W. ; Weisler R. H. ; Chang W. ; Paulsson B. ; Khan A. ; Calabrese J. R. J. Clin. Psychopharmacol. 2006, 26, 600. doi: 10.1097/01.jcp.0000248603.76231.b7
17	Chen S. ; Wang M. ; Jiang X. Chin. J. Chem. 2018, 36, 921. doi: 10.1002/cjoc.201800242
18	Lin D. Y. ; Zhang S.-Z. ; Block E. ; Katz L. C. Nature 2005, 434, 470. doi: 10.1038/nature03414
19	Kondo T. ; Mitsudo T.-A. Chem. Rev. 2000, 100, 3205. doi: 10.1021/cr9902749
20	Beletskaya I. P. ; Anikov V. P. Chem. Rev. 2011, 111, 1596. doi: 10.1021/cr100347k
21	Alvaro E. ; Hartwig J. F. J. Am. Chem. Soc. 2009, 131, 7858. doi: 10.1021/ja901793w
22	Fernandez-Rodriguez M. A. ; Shen Q. ; Hartwig J. F. J. Am. Chem. Soc. 2006, 128, 2180. doi: 10.1021/ja0580340
23	Ma D. ; Geng Q. ; Zhang H. ; Jiang Y. Angew. Chem. Int. Ed. 2010, 49, 1291. doi: 10.1002/anie.200905646
24	Cao H. ; Chen L. ; Liu J. ; Cai H. ; Deng H. ; Chen G. ; Yan C. ; Chen Y. RSC Adv. 2015, 5, 22356. doi: 10.1039/C5RA01342A
25	Ferraccioli R. Cur. Org. Synth. 2012, 9, 96. doi: 10.2174/157017912798889224
26	Liao Y. ; Peng Y. ; Qi H. ; Deng G.-J. ; Gong H. ; Li C.-J Chem. Commun. 2015, 51, 1031. doi: 10.1039/C4CC08370A
27	Chen X. ; Hao X.-S. ; Goodhue C. E. ; Yu J. -Q J. Am. Chem. Soc. 2006, 128, 6790. doi: 10.1021/ja061715q
28	Chu L. ; Yue X. ; Qing F. -L. Org. Lett. 2010, 12, 1644. doi: 10.1021/ol100449c
29	Fukuzawa S.-I. ; Shimizu E. ; Atsumi Y. ; Haga M. ; Ogata K. Tetrahedron Lett. 2009, 50, 2374. doi: 10.1016/j.tetlet.2009.02.214
30	Zhang S. ; Qian P. ; Zhang M. ; Hu M. ; Cheng J. J. Org. Chem. 2010, 75, 6732. doi: 10.1021/jo1014849
31	Zhou A.-X. ; Liu X.-Y. ; Yang K. ; Zhao S.-C. ; Liang Y.-M. Org. Biomol. Chem. 2011, 9, 5456. doi: 10.1039/C1OB05395G
32	Ranjit S. ; Lee R. ; Heryadi D. ; Shen C. ; Wu J. ; Zhang P. ; Huang K.-W. ; Liu X. J. Org. Chem. 2011, 76, 8999. doi: 10.1021/jo2017444
33	Alves D. ; Lara R. G. ; Contreira M. E. ; Radatz C. S. ; Duarte L. F. B. ; Perin G. Tetrahedron Lett. 2012, 53, 3364. doi: 10.1016/j.tetlet.2012.04.094
34	Dai C. ; Xu. Z. ; Huang. F. ; Yu Z. ; Gao Y.-F. J. Org. Chem. 2012, 77, 4414. doi: 10.1021/jo202624s
35	Rosario A. R. ; Casola K. K. ; Oliveira C. E. S. ; Zeni G. Adv. Synth. Catal. 2013, 355, 2960. doi: 10.1002/adsc.201300497
36	Zheng Z. ; Qi D. ; Shi L. Catal. Commun. 2015, 66, 83. doi: 10.1016/j.catcom.2015.03.023
37	Leroux F. ; Jeschke P. ; Schlosser M. Chem. Rev. 2005, 105, 827. doi: 10.1021/cr040075b
38	Boiko V. N. Beilstein J. Org. Chem. 2010, 6, 880. doi: 10.3762/bjoc.6.88
39	Jeschke P. Pest Manag. Sci. 2010, 66, 10. doi: 10.1002/ps.1829
40	Yang Y.-D. ; Azuma A. ; Tokunaga E. ; Yamasaki M. ; Shiro M. ; Shibata N. J. Am. Chem. Soc. 2013, 135, 8782. doi: 10.1021/ja402455f
41	Shao X. ; Wang X. ; Yang T. ; Lu L. ; Shen Q. Angew. Chem. Int. Ed. 2013, 52, 3457. doi: 10.1002/anie.201209817
42	Li Y. ; Ye Z. ; Bellman T. M. ; Chi T. ; Dai M. Org. Lett. 2015, 17, 2186. doi: 10.1021/acs.orglett.5b00782
43	Hu F. ; Shao X. ; Zhu D. ; Lu L. ; Shen Q. Angew. Chem. Int. Ed. 2014, 53, 6105. doi: 10.1002/anie.201402573
44	Bootwicha T. ; Liu X. ; Pluta R. ; AtodireseiI. ; Rueping M. Angew. Chem. Int. Ed. 2013, 52, 12856. doi: 10.1002/anie.201304957
45	Baert F. ; Colomb J. ; Billard T. Angew. Chem. Int. Ed. 2012, 51, 10382. doi: 10.1002/anie.201205156
46	Kang K. ; Xu C. ; Shen Q. Org. Chem. Front. 2014, 1, 294. doi: 10.1039/C3QO00068K
47	Liu J. ; Chu L. ; Qing F. -L. Org. Lett. 2013, 15, 894. doi: 10.1021/ol400032g
48	Wang Q. ; Qi Z. ; Xie F. ; Li X. Adv. Synth. Catal. 2015, 357, 355. doi: 10.1002/adsc.201400717
49	Yin G. ; Kalvet I. ; Schoenebeck F. Angew. Chem. Int. Ed. 2015, 54, 6809. doi: 10.1002/anie.201501617
50	Zhang C.-P. ; Vicic D. A. J. Am. Chem. Soc. 2012, 134, 183. doi: 10.1021/ja210364r
51	Zhu X.-L. ; Xu J.-H. ; Cheng D.-J. ; Zhao L.-J.; ; Liu X.-Y. ; Tan B. Org. Lett. 2014, 16, 2192. doi: 10.1021/ol5006888
52	Zhu L. ; Wang G. ; Gou Q. ; Xu Z. ; Zhang D. ; Wang R. Org. Lett. 2014, 16, 5390. doi: 10.1021/ol502624z
53	Ye K.-Y. ; Zhang X. ; Dai L.-X. ; You S.-L. J. Org. Chem. 2014, 79, 12106. doi: 10.1021/jo5019393
54	Tran L. D. ; Popov I. ; Daugulis O. J. Am. Chem. Soc. 2012, 134, 18237. doi: 10.1021/ja3092278
55	Yan X.-B. ; Gao P. ; Yang H.-B. ; Li Y.-X. ; Liu X.-Y. ; Liang Y.-M. Tetrahedron 2014, 70, 8730. doi: 10.1016/j.tet.2014.09.042
56	Shibahara F. ; Kanai T. ; Yamaguchi E. ; Kamei A. ; Yamauchi T. ; Murai T. Chem. Asian J. 2014, 9, 237. doi: 10.1002/asia.201300882
57	Chen C. ; Xu X.-H. ; Yang B. ; Qing F.-L. Org. Lett. 2014, 16, 3372. doi: 10.1021/ol501400u
58	Yang Y. ; Dong W. ; Gou Y. ; Rioux R. M. Green Chem. 2013, 15, 3170. doi: 10.1039/C3GC41330F
59	Lyons T. W. ; Sanford M. S. Chem. Rev. 2010, 110, 1147. doi: 10.1021/cr900184e
60	Daugulis O. ; Do H.-Q. ; Shabashov D. Acc. Chem. Res. 2009, 42, 1074. doi: 10.1021/ar9000058
61	He J. ; Wasa M. ; Chan K. S. L. ; Shao Q. ; Yu J. -Q. Chem. Rev. 2017, 117, 8754. doi: 10.1021/acs.chemrev.6b00622
62	Iwasaki M. ; Iyanaga M. ; Tsuchiya Y. ; Nishimura Y. ; Li W. ; Li Z. ; Nishihara Y. Chem. Eur. J. 2014, 20, 2459. doi: 10.1002/chem.201304717
63	Iwasaki M. ; Kaneshika W. ; Tsushiya Y. ; Nakajima K. ; Nishihara Y. J. Org. Chem. 2014, 79, 11330. doi: 10.1021/jo502274t
64	Zhang X..-S. ; Li G. ; Zhang X.-G. ; Zhang X.-H. Tetrahedron 2015, 71, 5458. doi: 10.1016/j.tet.2015.06.077
65	Xu C. ; Shen Q. Org. Lett. 2014, 16, 2046. doi: 10.1021/ol5006533
66	Yin W. ; Wang Z. ; Huang Y. Adv. Synth. Catal. 2014, 356, 2998. doi: 10.1002/adsc.201400362
67	Xiong H.-Y. ; Besset T. ; Cahard D. ; Pannecoucke X. J. Org. Chem. 2015, 80, 4204. doi: 10.1021/acs.joc.5b00505
68	Anbarasan P. ; Neumann H. ; Beller M. Chem. Commun. 2011, 47, 3233. doi: 10.1039/C0CC04405A
69	Saravanan P. ; Anbarasan P. Org. Lett. 2014, 16, 848. doi: 10.1021/ol4036209
70	Vásquez-Céspedes S. ; Ferry A. ; Candish L. ; Glorius F. Angew. Chem. Int. Ed. 2015, 54, 5772. doi: 10.1002/anie.201411997
71	Jiang Y. ; Liang G. ; Zhang C. ; Lohn T.-P. Eur. J. Org. Chem. 2016, 3326. doi: 10.1002/ejoc.201600588
72	Nakao Y. Chem. Rec. 2011, 11, 242. doi: 10.1002/tcr.201100023
73	Yan S.-Y. ; Liu Y.-J. ; Liu B. ; Liu Y.-H. ; Shi B.-F. Chem. Commun. 2015, 51, 4069. doi: 10.1039/C4CC10446C
74	Yang K. ; Wang Y. ; Chen X. ; Kadi A. A. ; Fun H.-K. ; Sun H. ; Zhang Y. ; Lu H. Chem. Commun. 2015, 51, 3582. doi: 10.1039/C4CC10431E
75	Lin C. ; Li D. ; Wang B. ; Yao J. ; Zhang Y. Org. Lett. 2015, 17, 1328. doi: 10.1021/acs.orglett.5b00337
76	Reddy V. P. ; Qiu R. ; Iwasaki T. ; Kambe N. Org. Biomol. Chem. 2015, 13, 6803. doi: 10.1039/C5OB00149H
77	Lin C. ; Yu W. ; Yao J. ; Wang B. ; Liu Z. ; Zhang Y. Org. Lett. 2015, 17, 1340. doi: 10.1021/acs.orglett.5b00471
78	Wang X. ; Qiu R. ; Yan C. ; Reddy V. P. ; Zhu L. ; Xu X. ; Yin S.-F. Org. Lett. 2015, 17, 1970. doi: 10.1021/acs.orglett.5b00706
79	Ye X. ; Petersen J. L. ; Shi X. Chem. Commun. 2015, 51, 7863. doi: 10.1039/C5CC01970B
80	Shen C. ; Zhang P. ; Sun Q. ; Bai S. ; Hor T. S. A. ; Liu X. Chem. Soc. Rev. 2015, 44, 291. doi: 10.1039/C4CS00239C
81	Yang Y. ; Hou W. ; Qin L. ; Du J. ; Feng H. ; Zhou B. ; Li Y. Chem. Eur. J. 2014, 20, 416. doi: 10.1002/chem.201303730
82	Wang Q. ; Xie F. ; Li X. J. Org. Chem. 2015, 80, 8361. doi: 10.1021/acs.joc.5b00940
83	Xie W. ; Li B. ; Wang B. J. Org. Chem. 2016, 81, 396. doi: 10.1021/acs.joc.5b01943
84	Maity S. ; Karmakar U. ; Samanta R. Chem. Commun. 2017, 53, 12197. doi: 10.1039/C7CC07086A
85	Gensch T. ; Klauck F. J. R. ; Glorius F. Angew. Chem. Int. Ed. 2016, 55, 11287. doi: 10.1002/anie.201605193
86	Mandal A. ; Dana S. ; Sahoo H. ; Grandhi G. S. ; Baidya M. Org. Lett. 2017, 19, 2430. doi: 10.1021/acs.orglett.7b00996
87	Zhang M. ; Zhang S. ; Pan C. ; Chen F. Synth. Commun. 2012, 42, 2844. doi: 10.1080/00397911.2011.569867
88	Ravi C. ; Mohan D. C. ; Adimurthy S. Org. Lett. 2014, 16, 2978. doi: 10.1021/ol501117z
89	Liu Y. ; Zhang Y. ; Hu C. ; Wan J.-P. ; Wen C. RSC Adv. 2014, 4, 35528. doi: 10.1039/C4RA05206D
90	Hiebel M.-A. ; Raboin S. B. Green Chem 2015, 17, 937. doi: 10.1039/C4GC01462F
91	Parumala S. K. R. ; Peddinti R. K. Green Chem 2015, 17, 4068. doi: 10.1039/C5GC00403A
92	Yang D. ; Sun P. ; Wei W. ; Meng L. ; He L. ; Fang B. ; Jiang W. ; Wang H. Org. Chem. Front. 2016, 3, 1457. doi: 10.1039/C6QO00407E
93	Chouldhury P. ; Roy B. ; Basu B. Asian J. Org. Chem. 2017, 6, 1569. doi: 10.1002/ajoc.201700275
94	Bai F. ; Zhang S. ; Wei L. ; Liu Y. Asian J. Org. Chem. 2018, 7, 371. doi: 10.1002/ajoc.201700677
95	Li B. ; Chen Z. ; Cao H. ; Zhao H. Org. Lett. 2018, 20, 3291. doi: 10.1021/acs.orglett.8b01168
96	Tang R.-Y. ; Xie Y.-X. ; Xie Y.-L. ; Xiang J.-N. ; Li J.-H. Chem. Commun. 2011, 47, 12867. doi: 10.1039/C1CC15397H
97	Zou L.-H. ; Reball J. ; Mottweiler J. ; Bolm C. Chem. Commun. 2012, 48, 11307. doi: 10.1039/C2CC36711D
98	Huang D. ; Chen J. ; Dan W. ; Ding J. ; Liu M. ; Wu H. Adv. Synth. Catal. 2012, 354, 2123. doi: 10.1002/adsc.201200227
99	Ge W. ; Wei Y. Green Chem. 2012, 14, 2066. doi: 10.1039/C2GC35337G
100	Guo S.-R. ; Yuan Y.-Q. ; Xiang J.-N. Org. Lett. 2013, 15, 4654. doi: 10.1021/ol402281f
101	Sang P. ; Chen Z. ; Zou J. ; Zhang Y. Green Chem. 2013, 15, 2096. doi: 10.1039/C3GC40724A
102	Azeredo J. ; Godoi M. ; Martins G. M. ; Silverira C. C. ; Braga A. L. J. Org. Chem. 2014, 79, 4125. doi: 10.1021/jo5000779
103	Gao Z. ; Zhu X. ; Zhang R. RSC Adv. 2014, 4, 19891. doi: 10.1039/C4RA01240B
104	Rafique J. ; Saba S. ; Franco M. S. ; Bettanin L. ; Schneider A. R. ; Silva L. T. ; Braga A. L. Chem. Eur. J. 2018, 24, 4173. doi: 10.1002/chem.201705404
105	Yu Y. ; Zhou Y. ; Song Z. ; Liang G. Org. Biomol. Chem. 2018, 16, 4958. doi: 10.1039/C8OB00948A
106	Wu Q. ; Zhao D. ; Qin X. ; Lan J. ; You J. Chem. Commun. 2011, 47, 9188. doi: 10.1039/C1CC13633J
107	Kumaraswamy G. ; Raju R. ; Narayanarao V. RSC Adv. 2015, 5, 22718. doi: 10.1039/C5RA00646E
108	Zhao W. ; Zhou A. ChemCatChem 2015, 7, 3464. doi: 10.1002/cctc.201500673
109	Jiang L. ; Yi W. ; Liu Q. Adv. Synth. Catal. 2016, 358, 3700. doi: 10.1002/adsc.201600651
110	Yang F.-L. ; Tian S.-K. Angew. Chem. Int. Ed. 2013, 52, 4929. doi: 10.1002/anie.201301437
111	Kang X. ; Yan R. ; Yu G. ; Pang X. ; Liu X. ; Li X. ; Xiang L. ; Huang G. J. Org. Chem. 2014, 79, 10605. doi: 10.1021/jo501778h
112	Bagdi A. K. ; Mitra S. ; Ghosh M. ; Hajra A. Org. Biomol. Chem. 2015, 13, 3314. doi: 10.1039/C5OB00033E
113	Zhao W. ; Xie P. ; Bian Z. ; Zhou A. ; Ge H. ; Zhang M. ; Ding Y. ; Zheng L. J. Org. Chem. 2015, 80, 9167. doi: 10.1021/acs.joc.5b01602
114	Rao H. ; Wang P. ; Wang J. ; Li Z. ; Sun X. ; Cao S. RSC Adv. 2014, 4, 49165. doi: 10.1039/C4RA08669D
115	Xiao F. ; Xie H. ; Liu S. ; Deng G.-J. Adv. Synth. Catal. 2014, 356, 364. doi: 10.1002/adsc.201300773
116	Ding Y. ; Wu W. ; Zhao W. ; Li Y. ; Xie P. ; Huang Y. ; Liu Y. ; Zhou A. Org. Biomol. Chem. 2016, 14, 1428. doi: 10.1039/C5OB02073E
117	Huang X. ; Wang S. ; Li B. ; Wang X. ; Ge Z. ; Li R. RSC Adv. 2015, 5, 22654. doi: 10.1039/C4RA17237J
118	Wang D. ; Zhang R. ; Lin S. ; Yan Z. ; Guo S. RSC Adv. 2015, 5, 108030. doi: 10.1039/C5RA24351C
119	Lin Y.-M. ; Lu G.-P. ; Wang G.-X. ; Yi W.-B. Adv. Synth. Catal. 2016, 358, 4100. doi: 10.1002/adsc.201600846
120	Gou Y.-J. ; Lu S. ; Tian L.-L. ; Huang E.-L. ; Hao X.-Q. ; Zhu X. ; Shao T. ; Song M.-P. J. Org. Chem. 2018, 83, 338. doi: 10.1021/acs.joc.7b02734
121	Liu C. ; Fan J. ; Wu M. ; Chen J. ; Xie M. Chin. J. Chem. 2018, 36, 819. doi: 10.1002/cjoc.201800164
122	Tudge M. ; Tamiya M. ; Savarin C. ; Humphrey G. Org. Lett. 2006, 8, 565. doi: 10.1021/ol052615c
123	Marcantoni E. ; Cipolletti R. ; Marsili L. ; Menichetti S. ; Properzi R. ; Viglianisi C. Eur. J. Org. Chem. 2013, 132. doi: 10.1002/ejoc.201201100
124	Lin Y. ; Yi W. Chin. J. Org. Chem. 2018, 38, 1207. doi: 10.6023/cjoc201711036
	林雅玫; 易文斌. 有机化学, 2018, 38, 1207. doi: 10.6023/cjoc201711036
125	Liu C. ; Ding L.-H. Org. Biomol. Chem. 2015, 13, 2251. doi: 10.1039/C4OB02575J
126	Qi H. ; Zhang T. ; Wan K. ; Lou M. J. Org. Chem. 2016, 81, 4262. doi: 10.1021/acs.joc.6b00636
127	Li Y. ; Zhu F. ; Wang Z. ; Wu X.-F. Chem. Asian J. 2016, 11, 3503. doi: 10.1002/asia.201601376
128	Fan W. ; Yang Z. ; Jiang B. ; Li G. Org. Chem. Front. 2017, 4, 1091. doi: 10.1039/C6QO00851H
129	Sun P. ; Yang D. ; Wei W. ; Jiang M. ; Wang Z. ; Zhang L. ; Zhang H. ; Zhang Z. ; Wang Y. ; Wang H. Green Chem. 2017, 19, 4785. doi: 10.1039/C7GC01891F
130	Yang X. ; Bao Y. ; Dai Z. ; Zhou Q. ; Yang F. Green Chem. 2018, 20, 3727. doi: 10.1039/C8GC01764F

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C―H官能化构建硫醚

C―H Functionalization Strategies for the Construction of Thioethers

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