REVIEWS

Research Progress in CS Bond Formation Reaction of Olefins with Organic Sulfur Reagents under Photocatalyst-Free and Non-Electrochemical Conditions

  • Bowen Wang ,
  • Yongjun Zhou ,
  • Shihe Luo ,
  • Xiaoyan Luo ,
  • Weiqing Chen ,
  • Shimin Yang ,
  • Zhaoyang Wang
Expand
  • a Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, Guangzhou Key Laboratory of Analytical Chemistry for Biomedicine, School of Chemistry, South China Normal University, Guangzhou 510006
    b Key Lab of Functional Molecular Engineering of Guangdong Province, South China University of Technology, Guangzhou 510640

Received date: 2020-06-29

  Revised date: 2020-07-24

  Online published: 2020-08-11

Supported by

the Science and Technology Project Scientific Special of Guangzhou City(201607010251); the Guangdong Provincial Science and Technology Project(2017A010103016); the Open Fund of the Key Laboratory of Functional Molecular Engineering of Guangdong Province(2017kf01)

Abstract

Olefin is an important synthetic synthon, and its concise and efficient transformation has been a research hotspot in the field of organic synthesis. In recent years, the C—S bond formation based on the olefin skeleton has received particular attention from scientists. Alkenes can react with common organic sulfur-containing reagents, including thiol, disulfide, sulfoxide, sulfonyl hydrazide, sulfonyl chloride, sodium sulfinate and other kinds of organosulfur reagents to build C—S bonds at the α-position or β-position of olefin to synthesize sulfide, sulfoxide or sulfone. Thus, according to the different classification of the used organosulfur reagents, the recent research progresses in C—S bond formation reaction of olefins with organic sulfur reagents under photocatalyst-free conditions and non-electrochemical method is summarized. In the future, among the researches on the C—S bond formation reactions of olefins with inexpensive organosulfur reagents, asymmetrical synthesis and various difunctionalizations are still promising directions.

Cite this article

Bowen Wang , Yongjun Zhou , Shihe Luo , Xiaoyan Luo , Weiqing Chen , Shimin Yang , Zhaoyang Wang . Research Progress in CS Bond Formation Reaction of Olefins with Organic Sulfur Reagents under Photocatalyst-Free and Non-Electrochemical Conditions[J]. Chinese Journal of Organic Chemistry, 2021 , 41(1) : 171 -184 . DOI: 10.6023/cjoc202006064

References

[1]
Trost B.M.; Kalnmals C.A. Chem.-Eur. J. 2019, 25, 11193.
[2]
Hofman K.; Liu N.-W.; Manolikakes G. Chem.-Eur. J. 2018, 24, 11852.
[3]
Mampuys P.; McElroy C.R.; Clark J.H.; Orru R.V.A.; Maes B.U.W. Adv. Synth. Catal. 2020, 362, 3.
[4]
Zhang S.N.; Yang S.H.; Huang L.H.; Zhao B.L.; Cheng K.; Qi C.Z. Chin. J. Org. Chem. 2015, 35, 2259. (in Chinese)
[4]
( 张诗浓, 杨胜虎, 黄乐浩, 赵保丽, 程凯, 齐陈泽, 有机化学, 2015, 35, 2259.).
[5]
Fang, Y.Y; Luo, Z.G.; Xu, X.M. RSC Adv. 2016, 6, 59661.
[6]
Huang G.B.; Li X.Y.; Luo J.R.; Luo Z.H.; Tan M.X. Chin. J. Org. Chem. 2019, 39, 617. (in Chinese)
[6]
( 黄国保, 李秀英, 罗金荣, 罗志辉, 谭明雄, 有机化学, 2019, 39, 617.).
[7]
Guo W.; Tao K.L.; Tan W.; Zhao M.M.; Zheng L.Y.; Fan X.L. Org. Chem. Front. 2019, 6, 2048.
[8]
Li Y.Q.; Fan Y.H. Synth. Commun. 2019, 49, 3227.
[9]
Cabrero-Antonino J.R.; Leyva-Perez A.; Corma A. Adv. Synth. Catal. 2012, 354, 678.
[10]
Mosaferi E.; Ripsman D.; Stephan D.W. Chem. Commun. 2016, 52, 8291.
[11]
Kucinski K.; Pawluc P.; Hreczycho G. Adv. Synth. Catal. 2015, 357, 3936.
[12]
Taniguchi N. ChemistrySelect 2018, 3, 6209.
[13]
Taniguchi N.; Kitayama K. Synlett 2018, 29, 2712.
[14]
Chun S.; Chung J.; Park J.E.; Chung Y.K. ChemCatChem 2016, 8, 2476.
[15]
Rosa C.H.; Peixoto M.L.B.; Rosa G.R.; Godoi B.; Galetto F.Z.; D'Oca M.G.M.; Godoi M. Tetrahedron Lett. 2017, 58, 3777.
[16]
Biermann U.; Metzger J.O. Eur. J. Org. Chem. 2018, 730.
[17]
Choudhuri K.; Mandal A.; Mal P. Chem. Commun. 2018, 54, 3759.
[18]
Lu Q.Q.; Wang H.M.; Peng P.; Liu C.; Huang Z.Y.; Luo Y.; Lei A.W. Org. Chem. Front. 2015, 2, 908.
[19]
Wang H.M.; Wang G.Y.; Lu Q.Q.; Chiang C.-W.; Peng P.; Zhou J.F.; Lei A.W. Chem.-Eur. J. 2016, 22, 14489.
[20]
Li C.S.; Li J.X.; Tan C.W.; Wu W.Q.; Jiang H.F. Org. Chem. Front. 2018, 5, 3158.
[21]
Zheng Y.; He Y.; Rong G.W.; Zhang X.L.; Weng Y.C.; Dong K.Y.; Xu X.F.; Mao J.C. Org. Lett. 2015, 17, 5444.
[22]
Cui H.H.; Liu X.X.; Wei W.; Yang D.S.; He C.L.; Zhang T.T.; Wang H. J. Org. Chem. 2016, 81, 2252.
[23]
Wang D.Y.; Yan Z.H.; Xie Q.H.; Zhang R.X.; Lin S.; Wang Y.X. Org. Biomol. Chem. 2017, 15, 1998.
[24]
Liu S.S.; Klussmann M. Chem. Commun. 2020, 56, 1557.
[25]
Zhou S.-F.; Pan X.Q.; Zhou Z.-H.; Shoberu A.; Zou J.-P. J. Org. Chem. 2015, 80, 3682.
[26]
Du B.N.; Wang Y.; Mei H.B.; Han J.L.; Pan Y. Adv. Synth. Catal. 2017, 359, 1684.
[27]
Zhao J.-J.; Tang M.; Zhang H.-H.; Xu M.-M.; Shi F. Chem. Commun. 2016, 52, 5953.
[28]
Hui Y.H.; Jiang J.; Wang W.T.; Chen W.L.; Cai Y.F.; Lin L.L.; Liu X.H.; Feng X.M. Angew. Chem., Int. Ed. 2010, 49, 4290.
[29]
Tian X.; Cassani C.; Liu Y.K.; Moran A.; Urakawa A.; Galzerano P.; Arceo E.; Melchiorre P. J. Am. Chem. Soc. 2011, 133, 17934.
[30]
Kitanosono T.; Sakai M.; Ueno M.; Kobayashi S. Org. Biomol. Chem. 2012, 10, 7134.
[31]
White J.D.; Shaw S. Chem. Sci. 2014, 5, 2200.
[32]
Chen J.A.; Meng S.X.; Wang L.M.; Tang H.M.; Huang Y. Chem. Sci. 2015, 6, 4184.
[33]
Farley A.J.M.; Sandford C.; Dixon D.J. J. Am. Chem. Soc. 2015, 137, 15992.
[34]
Huo C.D.; Wang Y.J.; Yuan Y.; Chen F.J.; Tang J. Chem. Commun. 2016, 52, 7233.
[35]
Xi H.; Deng B.C.; Zong Z.Z.; Lu S.L.; Li Z.P. Org. Lett. 2015, 17, 1180.
[36]
He L.; Guo H.; Li Y.-Z.; Du G.-F.; Dai B. Chem. Commun. 2014, 50, 3719.
[37]
Cong Z.-S.; Li Y.-G.; Du G.-F.; Gu C.-Z.; Dai B.; He L. Chem. Commun. 2017, 53, 13129.
[38]
Kawazoe S.; Yoshida K.; Shimazaki Y.; Oriyama T. Tetrahedron Lett. 2015, 56, 410.
[39]
Li Z.; Song G.Y.; He J.J.; Du Y.; Yang J.Y. J. Sulfur Chem. 2017, 38, 686.
[40]
Wei Q.; Hou W.D.; Liao N.; Peng Y.G. Adv. Synth. Catal. 2017, 359, 2364.
[41]
Wan J.-P.; Zhong S.S.; Xie L.L.; Cao X.J.; Liu Y.Y.; Wei L. Org. Lett. 2016, 18, 584.
[42]
Jiang Y.J.; Liang G.H.; Zhang C.; Loh T.-P. Eur. J. Org. Chem. 2016, 3326.
[43]
Siddaraju Y.; Prabhu K.R. J. Org. Chem. 2017, 82, 3084.
[44]
Orsi D.L.; Easley B.J.; Lick A.M.; Altman R.A. Org. Lett. 2017, 19, 1570.
[45]
Tamai T.; Ogawa A. J. Org. Chem. 2014, 79, 5028.
[46]
Tamai T.; Fujiwara K.; Higashimae S.; Nomoto A.; Ogawa A. Org. Lett. 2016, 18, 2114.
[47]
Yang X.-H.; Davison R.T.; Nie S.-Z.; Cruz F.A.; McGinnis T.M.; Dong V.M. J. Am. Chem. Soc. 2019, 141, 3006.
[48]
Yang X.-H.; Davison R.T.; Dong V.M. J. Am. Chem. Soc. 2018, 140, 10443.
[49]
Zhang Y.X.; Wong Z.R.; Wu X.X.; Lauw S.J.L.; Huang X.; Webster R.D.; Chi Y.G.R. Chem. Commun. 2016, 53, 184.
[50]
Wang L.L.; Yue H.L.; Yang D.S.; Cui H.H.; Zhu M.H.; Wang J.M.; Wei W.; Wang H. J. Org. Chem. 2017, 82, 6857.
[51]
Liang X.; Xiong M.T.; Zhu H.P.; Shen K.X.; Pan Y.J. J. Org. Chem. 2019, 84, 11210.
[52]
Wang Y.J.; Jiang W.; Huo C.D. J. Org. Chem. 2017, 82, 10628.
[53]
Singh A.K.; Chawla R.; Keshari T.; Yadav V.K.; Yadav L.D.S. Org. Biomol. Chem. 2014, 12, 8550.
[54]
Yang L.; Wen Q.; Xiao F.H.; Deng G.-J. Org. Biomol. Chem. 2014, 12, 9519.
[55]
Tu H.-Y.; Hu B.-L.; Deng C.-L.; Zhang X.-G. Chem. Commun. 2015, 51, 15558.
[56]
Liu Y.R.; Hu B.L.; Zhang X.G. Chin. J. Chem. 2017, 35, 307.
[57]
Sun K.; Lv Y.H.; Shi Z.D.; Mu S.Q.; Li C.H.; Wang X. Org. Biomol. Chem. 2017, 15, 5258.
[58]
Liu C.; Fang Y.; Wang S.-Y.; Ji S.-J. ACS Catal. 2019, 9, 8910.
[59]
Lin C.; Li D.Y.; Wang B.J.; Yao J.Z.; Zhang Y.H. Org. Lett. 2015, 17, 1328.
[60]
Liu S.-L.; Li X.-H.; Shi T.-H.; Yang G.-C.; Wang H.-L.; Gong J.-F.; Song M.-P. Eur. J. Org. Chem. 2017, 2280.
[61]
Shang Z.H.; Chen Q.Y.; Xing L.L.; Zhang Y.L.; Wait L.; Du Y.F. Adv. Synth. Catal. 2019, 361, 4926.
[62]
Liu C.; Fang Y.; Wang S.-Y.; Ji S.-J. Org. Lett. 2018, 20, 6112.
[63]
Tan Y.-H.; Li J.-X.; Hong W.-K.; Wang Z.-Y. Chin. J. Org. Chem. 2011, 31, 616. (in Chinese)
[63]
( 谭越河, 李建晓, 洪文坤, 汪朝阳, 有机化学, 2011, 31, 616.).
[64]
Mao C.-X.; Wang Z.-Y.; Tan Y.-H.; Xue F.-L. Chin. J. Org. Chem. 2011, 31, 1377. (in Chinese)
[64]
( 毛超旭, 汪朝阳, 谭越河, 薛福玲, 有机化学, 2011, 31, 1377.).
[65]
Liu J.; Chen W.; Wang L. RSC Adv. 2013, 3, 4723.
[66]
Cao L.; Luo S.-H.; Jiang K.; Hao Z.-F.; Wang B.-W.; Pang C.-M.; Wang Z.-Y. Org. Lett. 2018, 20, 4754.
[67]
Li J.; Rao W.D.; Wang S.-Y.; Ji S.-J. J. Org. Chem. 2019, 84, 11542.
[68]
Reddy R.J.; Kumar J.J.; Kumari A.H. Eur. J. Org. Chem. 2019, 3771.
[69]
Kong W.G.; Yu C.J.; An H.J.; Song Q.L. Org. Lett. 2018, 20, 4975.
[70]
Shyam P.K.; Son S.; Jang H.-Y. Eur. J. Org. Chem. 2017, 5025.
[71]
Son S.; Shyam P.K.; Park H.; Jeong I.; Jang H.-Y. Eur. J. Org. Chem. 2018, 3365.
[72]
Reddy R.J.; Kumari A.H.; Kumar J.J.; Nanubolu J.B. Adv. Synth. Catal. 2019, 361, 1587.
[73]
Shukla G.; Srivastava A.; Nagaraju A.; Raghuvanshi K.; Singh M.S. Adv. Synth. Catal. 2015, 357, 3969.
[74]
Wang B.-W.; Liu Y.; Hao Z.-F.; Hou J.-Q.; Li J.-Y.; Li S.-T.; Pan S.-H.; Zeng M.-H.; Wang Z.-Y. Chin. J. Org. Chem. 2018, 38, 1872. (in Chinese)
[74]
( 王柏文, 刘园, 郝志峰, 侯佳琦, 李健怡, 李舒婷, 潘思慧, 曾铭豪, 汪朝阳, 有机化学, 2018, 38, 1872.).
[75]
Yang K.; Gao J.-J.; Luo S.-H.; Wu H.-Q.; Pang C.-M.; Wang B.-W.; Chen X.-Y.; Wang Z.-Y. RSC Adv. 2019, 9, 19917.
[76]
Wu H.-Q.; Yang K.; Chen X.-Y.; Arulkumar M.; Wang N.; Chen S.-H.; Wang Z.-Y. Green Chem. 2019, 21, 3782.
[77]
Cao L.; Luo S.-H.; Wu H.-Q.; Chen L.-Q.; Jiang K.; Hao Z.-F.; Wang Z.-Y. Adv. Synth. Catal. 2017, 359, 2961.
[78]
Gao X.F.; Pan X.J.; Gao J.; Jiang H.F.; Yuan G.Q.; Li Y.W. Org. Lett. 2015, 17, 1038.
[79]
Hua J.W.; Xu J.Q.; Xu J.; Zhou B.C.; Zhang D.; Yang Z.; Fang Z.; Guo K. Eur. J. Org. Chem. 2019, 4056.
[80]
He R.F.; Chen X.W.; Li Y.B.; Liu Q.; Liao C.S.; Chen L.; Huang Y.B. J. Org. Chem. 2019, 84, 8750.
[81]
Ebule R.; Hammond G.B.; Xu B. Eur. J. Org. Chem. 2018, 4705.
[82]
Lan L.Y.; Gao Y.; Ding R.; Zhang T.; Liu Y.G.; Sun B.G.; Tian H.Y. Synth. Commun. 2019, 49, 539.
[83]
Gao X.F.; Pan X.J.; Gao J.; Huang H.W.; Yuan G.Q.; Li Y.W. Chem. Commun. 2015, 51, 210.
[84]
Jiang Y.J.; Loh T.-P. Chem. Sci. 2014, 5, 4939.
[85]
Shao A.L.; Gao M.; Chen S.T.; Wang T.; Lei A.W. Chem. Sci. 2017, 8, 2175.
[86]
Huang J.J.; Hu G.; An S.Y.; Chen D.D.; Li M.L.; Li P.F. J. Org. Chem. 2019, 84, 9758.
[87]
Yan J.J.; Pulis A.P.; Perry G.J.P.; Procter D.I. Angew. Chem., Int. Ed. 2019, 58, 15675.
[88]
Haut F.-L.; Habiger C.; Speck K.; Wurst K.; Mayer P.; Korber J.N.; Muller T.; Magauer T. J. Am. Chem. Soc. 2019, 141, 13352.
[89]
Xu X.M.; Li J.Z.; Wang Z.L. Chin. J. Org. Chem. 2020, 40, 886. (in Chinese)
[89]
( 徐鑫明, 李家柱, 王祖利, 有机化学, 2020, 40, 886.).
[90]
Deng L.L.; Liu Y.Y. ACS Omega 2018, 3, 11890.
[91]
Wang F.-X.; Tian S.-K. J. Org. Chem. 2015, 80, 12697.
[92]
Yang F.-L.; Wang F.-X.; Wang T.-T.; Wang Y.-J.; Tian S.-K. Chem. Commun. 2014, 50, 2111.
[93]
Yang F.-L.; Gui Y.; Yu B.-K.; Jin Y.-X.; Tian S.-K. Adv. Synth. Catal. 2016, 358, 3368.
[94]
Singh R.; Allam B.K.; Singh N.; Kumari K.; Singh S.K.; Singh K.N. Org. Lett. 2015, 17, 2656.
[95]
Aegurla B.; Peddinti R.K. Asian J. Org. Chem. 2018, 7, 946.
[96]
Liu C.R.; Ding L.H.; Guo G.; Liu W.W. Eur. J. Org. Chem. 2016, 910.
[97]
Wei W.; Liu C.L.; Yang D.S.; Wen J.W.; You J.M.; Suo Y.R.; Wang H. Chem. Commun. 2013, 49, 10239.
[98]
Wan X.; Sun K.; Zhang G.S. Sci. China: Chem. 2017, 60, 353.
[99]
Tang Y.C.; Fan Y.Y.; Gao H.J.; Li X.Q.; Xu X.S. Tetrahedron Lett. 2015, 56, 5616.
[100]
Tang Y.C.; Zhang Y.; Wang K.F.; Li X.Q.; Xu X.S.; Du X.H. Org. Biomol. Chem. 2015, 13, 7084.
[101]
Chen W.T.; Liu X.Y.; Chen E.; Chen B.H.; Shao J.A.; Yu Y.P. Org. Chem. Front. 2017, 4, 1162.
[102]
Terent'ev A.O.; Mulina O.M.; Pirgach D.A.; Demchuk D.V.; Syroeshkin M.A.; Nikishin G.I. RSC Adv. 2016, 6, 93476.
[103]
Choudhuri K.; Achar T.K.; Mal P. Adv. Synth. Catal. 2017, 359, 3566.
[104]
Sun K.; Lv Y.H.; Zhu Z.H.; Jiang Y.Q.; Qi J.J.; Wu H.K.; Zhang Z.G.; Zhang G.S.; Wang X. RSC Adv. 2015, 5, 50701.
[105]
Xu R.; Li Z.P. Tetrahedron Lett. 2018, 59, 3942.
[106]
Wang B.; Tang L.; Liu L.Y.; Li Y.N.; Yang Y.; Wang Z.Y. Green Chem. 2017, 19, 5794.
[107]
Wang D.Y.; Zhang R.X.; Lin S.; Yan Z.H.; Guo S.M. Synlett 2016, 27, 2003.
[108]
Ni J.X.; Jiang Y.; An Z.Y.; Lan J.F.; Yan R.L. Chem. Commun. 2019, 55, 7343.
[109]
Jiang L.Q.; Ding T.Q.; Yi W.-B.; Zeng X.; Zhang W. Org. Lett. 2018, 20, 2236.
[110]
Wei J.J.; Liang S.S.; Jiang L.Q.; Mumtaz Y.; Yi W.-B. J. Org. Chem. 2020, 85, 977.
[111]
Xia Y.Y.; Chen X.L.; Qu L.B.; Sun K.; Xia X.Y.; Fu W.K.; Chen X.; Yang Y.K.; Zhao Y.F.; Li C.J. Asian J. Org. Chem. 2016, 5, 878.
[112]
Lai M.; Wu Z.Y.; Li S.-J.; Wei D.H.; Zhao M.Q. J. Org. Chem. 2019, 84, 11135.
[113]
Zhu R.; Buchwald S.L. J. Am. Chem. Soc. 2015, 137, 8069.
[114]
Shi J.; Tang X.-D.; Wu Y.-C.; Li H.-N.; Song L.-J.; Wang Z.-Y. Eur. J. Org. Chem. 2015, 1193.
[115]
Lin Y.-M.; Lu G.-P.; Wang G.-X.; Yi W.-B. J. Org. Chem. 2017, 82, 382.
[116]
Wang D.Y.; Zhang R.X.; Ning W.; Yan Z.H.; Lin S. Org. Biomol. Chem. 2016, 14, 5136.
[117]
Wang B.-W.; Jiang K.; Li J.-X.; Luo S.-H.; Wang Z.-Y.; Jiang H.-F. Angew. Chem., Int. Ed. 2020, 59, 2338.
[118]
Shi J.; Tang X.-D.L; Wu Y.-C.; Fang J.-F.; Cao L.; Chen X.-Y.; Wang Z.-Y. RSC Adv. 2016, 6, 25651.
[119]
Zhang N.; Yang D.S.; Wei W.; Yuan L.; Cao Y.J.; Wang H. RSC Adv. 2015, 5, 37013.
[120]
Hua L.-N.; Li H.; Qing F.-L.; Huang Y.G.; Xu X.-H. Org. Biomol. Chem. 2016, 14, 8443.
[121]
Wu H.-Q.; Luo S.-H.; Cao L.; Shi H.-N.; Wang B.-W.; Wang Z.-Y. Asian J. Org. Chem. 2018, 7, 2479.
[122]
Wu H.-Q.; Yang K.; Luo S.-H.; Wu X.-Y.; Wang N.; Chen S.-H.; Wang Z.-Y. Eur. J. Org. Chem. 2019, 28, 4572.
[123]
Wu Y.-C.; Luo S.-H.; Mei W.-J.; Cao L.; Wu H.-Q.; Wang Z.-Y. Eur. J. Med. Chem. 2017, 139, 84.
[124]
Wu Y.-C.; Cao L.; Mei W.-J.; Wu H.-Q.; Luo S.-H.; Zhan H.-Y.; Wang Z.-Y. Chem. Biol. Drug Des. 2018, 92, 1232.
[125]
Luo S.-H.; Yang K.; Lin J.-Y.; Gao J.-J.; Wu X.-Y.; Wang Z.-Y. Org. Biomol. Chem. 2019, 17, 5138.
[126]
Cao L.; Li J.-X.; Wu H.-Q.; Jiang K.; Hao Z.-F.; Luo S.-H.; Wang Z.-Y. ACS Sustainable Chem. Eng. 2018, 6, 4147.
[127]
Ke M.L.; Huang G.X.; Ding L.; Fang J.J.; Chen F.-E. ChemCatChem 2019, 11, 4720.
[128]
Wang L.-J.; Chen M.M.; Qi L.; Xu Z.D.; Li W. Chem. Commun. 2017, 53, 2056.
[129]
Kariya A.; Yamaguchi T.; Nobuta T.; Tada N.; Miura T.; Itoh A. RSC Adv. 2014, 4, 13191.
[130]
Chawla R.; Singh A.K.; Yadav L.D.S. Eur. J. Org. Chem. 2014, 2032.
[131]
Zeng K.; Chen L.; Chen Y.; Liu Y.P.; Zhou Y.B.; Au C.-T.; Yin S.-F. Adv. Synth. Catal. 2017, 359, 841.
[132]
Xiong Y.; Sun Y.W.; Zhang G.Z. Org. Lett. 2018, 20, 6250.
[133]
Kramer P.; Halaczkiewicz M.; Sun Y.; Kelm H.; Manolikakes G. J. Org. Chem. 2020, 85, 3617.
[134]
Gao W.-C.; Cheng Y.-F.; Shang Y.-Z.; Chang H.-H.; Li X.; Zhou R.; Qiao Y.; Wei W.-L. J. Org. Chem. 2018, 83, 11956.
[135]
Shen T.; Yuan Y.Z.; Song S.; Jiao N. Chem. Commun. 2014, 50, 4115.
[136]
Wei W.; Wen J.W.; Yang D.S.; Du J.; You J.M.; Wang H. Green Chem. 2014, 16, 2988.
[137]
Chu X.-Q.; Meng H.; Xu X.-P.; Ji S.-J. Chem.-Eur. J. 2015, 21, 11359.
[138]
Wei W.; Wen J.W.; Yang D.S.; Wu M.; You J.M.; Wang H. Org. Biomol. Chem. 2014, 12, 7678.
[139]
Lu Q.Q.; Zhang J.; Wei F.L.; Qi Y.; Wang H.M.; Liu Z.L.; Lei A.W. Angew. Chem., Int. Ed. 2013, 52, 7156.
[140]
Yuan Z.L.; Wang H.-Y.; Mu X.; Chen P.H.; Guo Y.-L.; Liu G.S. J. Am. Chem. Soc. 2015, 137, 2468.
[141]
Liu X.; An R.; Zhang X.L.; Luo J.; Zhao X.D. Angew. Chem., Int. Ed. 2016, 55, 5846.
[142]
Luo J.; Liu Y.N.; Zhao X.D. Org. Lett. 2017, 19, 3434.
[143]
Zhang J.J.; Yang J.-D.; Zheng H.-L.; Xue X.-S.; Mayr H.; Cheng J.-P. Angew. Chem., Int. Ed. 2018, 57, 12690.
[144]
Luo J.; Cao Q.X.; Cao X.H.; Zhao X.D. Nat. Commun. 2018, 9, 527.
[145]
Liu X.; Lang Y.Y.; Ji J.Y.; Luo J.; Zhao X. J. Am. Chem. Soc. 2018, 140, 4782.
[146]
Zhang P.P.; Li M.; Xue X.-S.; Xu C.-F.; Zhao Q.C.; Liu Y.F.; Wang H.Y.; Guo Y.L.; Lu L.; Shen Q.L. J. Org. Chem. 2016, 81, 7486.
[147]
Yoo J.; Ha H.-J.; Kim B.; Cho C.-W. J. Org. Chem. 2020, 85, 7077.
[148]
Tian H.; Yu J.P.; Yang H.J.; Zhu C.J.; Fu H. Adv. Synth. Catal. 2016, 358, 1794.
[149]
Xiao Q.; He Q.J.; Li J.C.; Wang J. Org. Lett. 2015, 17, 6090.
[150]
Jia Y.M.; Qin H.M.; Wang N.; Jiang Z.-X.; Yang Z.G. J. Org. Chem. 2018, 83, 2808.
[151]
Sicignano M.; Rodriguez R.I.; Capaccio V.; Borello F.; Cano R.; De Riccardis F.; Bernardi L.; Diaz-Tendero S.; Della Sala G.; Aleman J. Org. Biomol. Chem. 2020, 18, 2914.
[152]
Jin M.Y.; Li J.C.; Huang R.K.; Zhou Y.X.; Chung L.W.; Wang J. Chem. Commun. 2018, 54, 4581.
[153]
Liang Y.Y.; Zhao X.D. ACS Catal. 2019, 9, 6896.
[154]
Xu C.F.; Shen Q.L. Org. Lett. 2015, 17, 4561.
[155]
Yang T.; Lu L.; Shen Q.L. Chem. Commun. 2015, 51, 5479.
[156]
Luo J.; Zhu Z.C.; Liu Y.N.; Zhao X.D. Org. Lett. 2015, 17, 3620.
[157]
Zhu Z.C.; Luo J.; Zhao X.D. Org. Lett. 2017, 19, 4940.
[158]
Song T.; Zhao X.M.; Wang X.L. J. Org. Chem. 2019, 84, 15648.
[159]
Nguyen T.B. Adv. Synth. Catal. 2020, 362, 3448.
[160]
Yin F.; Wang X.-S. Org. Lett. 2014, 16, 1128.
[161]
Cheng Z.-F.; Tao T.-T.; Feng Y.-S.; Tang W.-K.; Xu J.; Dai J.-J.; Xu H.-J. J. Org. Chem. 2018, 83, 499.
[162]
Meng Y.Y.; Wang M.; Jiang X.F. Angew. Chem., Int. Ed. 2020, 59, 1346.
[163]
Cui H.H.; Wei W.; Yang D.S.; Zhang Y.L.; Zhao H.J.; Wang L.L.; Wang H. Green Chem. 2017, 19, 3520.
[164]
Wang J.L.; Huang B.B.; Yang C.; Xia W.J. Chem. Commun. 2019, 55, 11103.
[165]
Wu J.; Zhang Y.L.; Gong X.C.; Meng Y.G.; Zhu C.Y. Org. Biomol. Chem. 2019, 17, 3507.
[166]
Gallhof M.; Kell L.; Brasholz M. Chem.-Eur. J. 2020, 26, 1772.
[167]
Wang Y.; Deng L.L.; Mei H.B.; Du B.N.; Han J.L.; Pan Y. Green Chem. 2018, 20, 3444.
[168]
Li D.D.; Li S.B.; Peng C.; Lu L.J.; Wang S.C.; Wang P.; Chen Y.-H.; Cong H.J.; Lei A.W. Chem. Sci. 2019, 10, 2791.
[169]
Luo M.-J.; Liu B.; Li Y.; Hu M.; Li J.-H. Adv. Synth. Catal. 2019, 361, 1538.
[170]
Zhu H.-D.; Hao W.-J.; Zhu C. - F.; Guo C.; Tu S.-J.; Jiang B. Org. Lett. 2020, 22, 4471.
[171]
Tang N.N.; Shao X.; Wang M.Y.; Wu X.X.; Zhu C. Acta Chim. Sinica 2019, 77, 922. (in Chinese)
[171]
( 汤娜娜, 邵鑫, 王明扬, 吴新鑫, 朱晨, 化学学报, 2019, 77, 922.).
[172]
Yang J.H.; Fu X.B.; Lu Z.H.; Zhu G.G. Acta Chim. Sinica 2019, 77, 901. (in Chinese)
[172]
( 杨俊航, 傅晓波, 卢增辉, 朱钢国, 化学学报, 2019, 77, 901.).
Outlines

/