Recent Metal-Catalyzed Methods for Thioether Synthesis

Valentin J. Geiger; Regina M. Oechsner; Paul H. Gehrtz; Ivana Fleischer

doi:10.1055/a-1914-1231

Synthesis, Table of Contents

Synthesis 2022; 54(23): 5139-5167
DOI: 10.1055/a-1914-1231

review

Recent Metal-Catalyzed Methods for Thioether Synthesis

Authors

Valentin J. Geiger
Regina M. Oechsner
Paul H. Gehrtz
Ivana Fleischer ∗

Abstract

All articles of this category

Dedicated to Prof. Dr. Štefan Toma on the occasion of his 85^th birthday

Abstract

This review summarizes the more recent methods (since 2015) for the synthesis of thioethers using homogeneous metals as catalysts. The thioether moiety can be found in numerous compounds for pharmaceutical, agricultural, or material applications and it is therefore important to develop new, efficient methods for their synthesis. The recent efforts in this field focus on the use of non-precious metal catalysts, as well as on the development of new bond-forming processes.

1 Introduction

2 Cross-Couplings

3 C–H Activation

4 Hydrothiolation

5 Carbothiolation

6 Miscellaneous

7 Conclusion

Key words

thioethers - sulfides - homogeneous catalysis - coupling - hydrothiolation - C–H activation - decarbonylation

Full Text

References

References
1 Current address: Merck Healthcare KGaA, Frankfurter Straße 250, 64293 Darmstadt, Germany.
2 Norgard NB, Hann CL, Dale GL. Clin. Appl. Thromb./Hemostasis 2009; 15: 177
3 Bang-Andersen B, Ruhland T, Jørgensen M, Smith G, Frederiksen K, Jensen KG, Zhong H, Nielsen SM, Hogg S, Mørk A, Stensbøl TB. J. Med. Chem. 2011; 54: 3206
4 Ilardi EA, Vitaku E, Njardarson JT. J. Med. Chem. 2014; 57: 2832
5 Scott KA, Njardarson JT. Top. Curr. Chem. 2018; 376: 5
6 Hill HW. Jr, Brady DG. Polym. Eng. Sci. 1976; 16: 831
7 Hilton HW, Nomura NS, Yauger WL, Kameda SS. J. Agric. Food. Chem. 1974; 22: 578
8 Dörwald FZ. Lead Optimization for Medicinal Chemists . Wiley-VCH; Weinheim: 2012: 100
9 McCracken RO, Lipkowitz KB. J. Parasitol. 1990; 76: 180
10 The values depicted in Figure 2 were computed using chemaxon.
11 Beno BR, Yeung K.-S, Bartberger MD, Pennington LD, Meanwell NA. J. Med. Chem. 2015; 58: 4383
12 Honda T, Tajima H, Kaneko Y, Ban M, Inaba T, Takeno Y, Okamoto K, Aono H. Bioorg. Med. Chem. Lett. 2008; 18: 2939
13 Tagaki W. In Organic Chemistry of Sulfur . Oae S. Springer US; Boston MA: 1977: 231
14 Cheng J.-H, Ramesh C, Kao H.-L, Wang Y.-J, Chan C.-C, Lee C.-F. J. Org. Chem. 2012; 77: 10369

15a Leuckart R. J. Prakt. Chem. 1890; 41: 179
15b Koziakov D, Majek M, Jacobi von Wangelin A. Org. Biomol. Chem. 2016; 14: 11347

16 Sinha AK, Equbal D. Asian J. Org. Chem. 2019; 8: 32
17 Massi A, Nanni D. Org. Biomol. Chem. 2012; 10: 3791
18 Sundaravelu N, Sangeetha S, Sekar G. Org. Biomol. Chem. 2021; 19: 1459
19 Wimmer A, König B. Beistein J. Org. Chem. 2018; 14: 54

20a Ghaderi A. Tetrahedron 2016; 72: 4758
20b Lee C.-F, Liu Y.-C, Badsara SS. Chem. Asian J. 2014; 9: 706
20c Eichman CC, Stambuli JP. Molecules 2011; 16: 590
20d Beletskaya IP, Ananikov VP. Chem. Rev. 2011; 111: 1596
20e Bichler P, Love JA. In C–X Bond Formation . Vigalok A. Springer; Heidelberg: 2010: 39
20f Li J, Yang S, Wu W, Jiang H. Org. Chem. Front. 2020; 7: 1395

21 Kosugi M, Shimizu T, Migita T. Chem. Lett. 1978; 7: 13
22 Migita T, Shimizu T, Asami Y, Shiobara J.-i, Kato Y, Kosugi M. Bull. Chem. Soc. Jpn. 1980; 53: 1385
23 Fernández-Rodríguez MA, Shen Q, Hartwig JF. J. Am. Chem. Soc. 2006; 128: 2180
24 Xu J, Liu RY, Yeung CS, Buchwald SL. ACS Catal. 2019; 9: 6461
25 Itoh T, Mase T. Org. Lett. 2004; 6: 4587

26a Chekal B, Damon D, LaFrance D, Leeman K, Mojica C, Palm A, St Pierre M, Sieser J, Sutherland K, Vaidyanathan R, Van Alsten J, Vanderplas B, Wager C, Weisenburger G, Withbroe G, Yu S. Org. Process Res. Dev. 2015; 19: 1944
26b Al-Shuaeeb RA. A, Galvani G, Bernadat G, Brion J.-D, Alami M, Messaoudi S. Org. Biomol. Chem. 2015; 13: 10904

27 Scattolin T, Senol E, Yin G, Guo Q, Schoenebeck F. Angew. Chem. Int. Ed. 2018; 57: 12425
28 Farmer JL, Pompeo M, Lough AJ, Organ MG. Chem. Eur. J. 2014; 20: 15790
29 Jones AC, Nicholson WI, Smallman HR, Browne DL. Org. Lett. 2020; 22: 7433
30 Bandaru SS. M, Bhilare S, Cardozo J, Chrysochos N, Schulzke C, Sanghvi YS, Gunturu KC, Kapdi AR. J. Org. Chem. 2019; 84: 8921
31 Velasco N, Virumbrales C, Sanz R, Suárez-Pantiga S, Fernández-Rodríguez MA. Org. Lett. 2018; 20: 2848
32 Talukder MM, Miller JT, Cue JM. O, Udamulle CM, Bhadran A, Biewer MC, Stefan MC. Organometallics 2021; 40: 83

33a Zhao T, Liang F, Cai M, Chen J, Kang C, Wang H, Wu Q. Asian J. Org. Chem. 2020; 9: 214
33b Oechsle P, Hou P, Flörke U, Paradies J. Adv. Synth. Catal. 2016; 358: 3770
33c Oechsle P, Flörke U, Egold H, Paradies J. Chem. Eur. J. 2016; 22: 18559
33d Hou P, Oechsle P, Kuckling D, Paradies J. Macromol. Rapid Commun. 2020; 41: 2000067

34 Abidi N, Schmink JR. J. Org. Chem. 2015; 80: 4123

35a Chen L, Noory Fajer A, Yessimbekov Z, Kazemi M, Mohammadi M. J. Sulfur Chem. 2019; 40: 451
35b Lee C.-F. Phosphorus, Sulfur Silicon Relat. Elem. 2019; 194: 678
35c Sambiagio C, Marsden SP, Blacker AJ, McGowan PC. Chem. Soc. Rev. 2014; 43: 3525

36a Yamamoto T, Sekine Y. Can. J. Chem. 1984; 62: 1544
36b Lindley J. Tetrahedron 1984; 40: 1433

37a Kalinin AV, Bower JF, Riebel P, Snieckus V. J. Org. Chem. 1999; 64: 2986
37b Palomo C, Oiarbide M, López R, Gómez-Bengoa E. Tetrahedron Lett. 2000; 41: 1283
37c Bates CG, Gujadhur RK, Venkataraman D. Org. Lett. 2002; 4: 2803

38 Thomas AM, Asha S, Sindhu KS, Anilkumar G. Tetrahedron Lett. 2015; 56: 6560
39 Bakare SP, Patil M. New J. Chem. 2022; 46: 6283
40 Chen C.-W, Chen Y.-L, Reddy DM, Du K, Li C.-E, Shih B.-H, Xue Y.-J, Lee C.-F. Chem. Eur. J. 2017; 23: 10087
41 Nowrouzi N, Abbasi M, Latifi H. Chin. J. Catal. 2016; 37: 1550
42 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
43 Yuan X, Kou Y, Yu L, Zhang Z.-X, Xue W. Org. Chem. Front. 2015; 2: 1604
44 Liu Y, Lam LY, Ye J, Blanchard N, Ma C. Adv. Synth. Catal. 2020; 362: 2326
45 Chen S, Zhang M, Liao X, Weng Z. J. Org. Chem. 2016; 81: 7993
46 Sangeetha S, Muthupandi P, Sekar G. Org. Lett. 2015; 17: 6006

47a Sangeetha S, Sekar G. Org. Lett. 2019; 21: 75
47b Sundaravelu N, Sekar G. Chem. Commun. 2020; 56: 8826
47c Sundaravelu N, Singha T, Nandy A, Sekar G. Chem. Commun. 2021; 57: 4512
47d Sangeetha S, Sekar G. Chem. Commun. 2020; 56: 10906
47e Sundaravelu N, Sekar G. Org. Lett. 2019; 21: 6648
47f Sangeetha S, Sekar G. Org. Lett. 2017; 19: 1670
47g Muthupandi P, Sundaravelu N, Sekar G. J. Org. Chem. 2017; 82: 1936

48 Zhou L, Chen Z, Li J, Li B. RSC Adv. 2021; 11: 34071
49 Cristau HJ, Chabaud B, Chêne A, Christol H. Synthesis 1981; 892
50 Kanchana US, Diana EJ, Mathew TV. Asian J. Org. Chem. 2022; 11: e202200038

51a Ananikov VP. ACS Catal. 2015; 5: 1964
51b Tasker SZ, Standley EA, Jamison TF. Nature 2014; 509: 299
51c Diccianni JB, Diao T. Trends Chem. 2019; 1: 830

52a Wellala NP. N, Guan H. Org. Biomol. Chem. 2015; 13: 10802
52b Guo F.-J, Sun J, Xu Z.-Q, Kühn FE, Zang S.-L, Zhou M.-D. Catal. Commun. 2017; 96: 11

53 Yu TY, Pang H, Cao Y, Gallou F, Lipshutz BH. Angew. Chem. Int. Ed. 2021; 60: 3708
54 Sikari R, Sinha S, Das S, Saha A, Chakraborty G, Mondal R, Paul ND. J. Org. Chem. 2019; 84: 4072
55 Yin G, Kalvet I, Englert U, Schoenebeck F. J. Am. Chem. Soc. 2015; 137: 4164
56 Zhang C.-P, Vicic DA. J. Am. Chem. Soc. 2012; 134: 183
57 Kalvet I, Guo Q, Tizzard GJ, Schoenebeck F. ACS Catal. 2017; 7: 2126
58 Jones KD, Power DJ, Bierer D, Gericke KM, Stewart SG. Org. Lett. 2018; 20: 208
59 Gehrtz PH, Geiger V, Schmidt T, Srsan L, Fleischer I. Org. Lett. 2019; 21: 50
60 Oechsner RM, Wagner JP, Fleischer I. ACS Catal. 2022; 12: 2233
61 Martín MT, Marín M, Maya C, Prieto A, Nicasio MC. Chem. Eur. J. 2021; 27: 12320
62 Serrano-Becerra JM, Valdés H, Canseco-González D, Gómez-Benítez V, Hernández-Ortega S, Morales-Morales D. Tetrahedron Lett. 2018; 59: 3377
63 Liu X, Cao Q, Xu W, Zeng M.-T, Dong Z.-B. Eur. J. Org. Chem. 2017; 2017: 5795
64 Zhang J, Wang S, Zhang Y, Feng Z. Asian J. Org. Chem. 2020; 9: 1519
65 Correa A, Carril M, Bolm C. Angew. Chem. Int. Ed. 2008; 47: 2880
66 Buchwald SL, Bolm C. Angew. Chem. Int. Ed. 2009; 48: 5586
67 Sindhu KS, Abi TG, Mathai G, Anilkumar G. Polyhedron 2019; 158: 270
68 Hu W, Zhang S. J. Org. Chem. 2015; 80: 6128
69 Duan F.-F, Song S.-Q, Xu R.-S. Chem. Commun. 2017; 53: 2737
70 Arisawa M, Suzuki T, Ishikawa T, Yamaguchi M. J. Am. Chem. Soc. 2008; 130: 12214
71 Wong Y.-C, Jayanth TT, Cheng C.-H. Org. Lett. 2006; 8: 5613
72 Liu T.-J, Yi C.-L, Chan C.-C, Lee C.-F. Chem. Asian J. 2013; 8: 1029
73 Reddy VP, Swapna K, Kumar AV, Rao KR. J. Org. Chem. 2009; 74: 3189
74 Thankachan AP, Sindhu KS, Krishnan KK, Anilkumar G. RSC Adv. 2015; 5: 32675

75a Chan DM. T, Monaco KL, Wang R.-P, Winters MP. Tetrahedron Lett. 1998; 39: 2933
75b Evans DA, Katz JL, West TR. Tetrahedron Lett. 1998; 39: 2937
75c Lam PY. S, Clark CG, Saubern S, Adams J, Winters MP, Chan DM. T, Combs A. Tetrahedron Lett. 1998; 39: 2941

76a Luo P.-S, Wang F, Li J.-H, Tang R.-Y, Zhong P. Synthesis 2009; 921
76b Xu H.-J, Zhao Y.-Q, Feng T, Feng Y.-S. J. Org. Chem. 2012; 77: 2878

77a Barcellos AM, Sacramento M, da Costa GP, Perin G, João Lenardão E, Alves D. Coord. Chem. Rev. 2021; 442: 214012
77b Chen J.-Q, Li J.-H, Dong Z.-B. Adv. Synth. Catal. 2020; 362: 3311

78a Cheng Y, Liu X, Dong Z.-B. Eur. J. Org. Chem. 2018; 2018: 815
78b Liu X, Zhang S.-B, Zhu H, Cheng Y, Peng H.-Y, Dong Z.-B. Eur. J. Org. Chem. 2018; 2018: 4483
78c Liu X, Dong Z.-B. J. Org. Chem. 2019; 84: 11524
78d Rostami A, Rostami A, Ghaderi A. J. Org. Chem. 2015; 80: 8694
78e Wang T.-T, Yang F.-L, Tian S.-K. Adv. Synth. Catal. 2015; 357: 928

79 Qiao Z, Ge N, Jiang X. Chem. Commun. 2015; 51: 10295
80 Yoshida S, Sugimura Y, Hazama Y, Nishiyama Y, Yano T, Shimizu S, Hosoya T. Chem. Commun. 2015; 51: 16613
81 Kanemoto K, Sugimura Y, Shimizu S, Yoshida S, Hosoya T. Chem. Commun. 2017; 53: 10640

82a Singh R, Allam BK, Singh N, Kumari K, Singh SK, Singh KN. Adv. Synth. Catal. 2015; 357: 1181
82b Bhowmik A, Yadav M, Fernandes RA. Org. Biomol. Chem. 2020; 18: 2447

83 Khakyzadeh V, Rostami A, Veisi H, Shirmardi Shaghasemi B, Reimhult E, Luque R, Xia Y, Darvishi S. Org. Biomol. Chem. 2019; 17: 4491
84 Wang C, Zhang Z, Tu Y, Li Y, Wu J, Zhao J. J. Org. Chem. 2018; 83: 2389

85a Guo L, Rueping M. Acc. Chem. Res. 2018; 51: 1185
85b Lu H, Yu T.-Y, Xu P.-F, Wei H. Chem. Rev. 2021; 121: 365
85c Liu C, Szostak M. ChemCatChem 2021; 13: 4878

86a Shen C, Zhang P, Sun Q, Bai S, Hor TS. A, Liu X. Chem. Soc. Rev. 2015; 44: 291
86b Sharma R, Yadav MR. Org. Biomol. Chem. 2021; 19: 5476

87 Hirschbeck V, Gehrtz PH, Fleischer I. Chem. Eur. J. 2018; 24: 7092

88a Osakada K, Yamamoto T, Yamamoto A. Tetrahedron Lett. 1987; 28: 6321
88b Wenkert E, Chianelli D. J. Chem. Soc., Chem. Commun. 1991; 627

89 Ichiishi N, Malapit CA, Woźniak Ł, Sanford MS. Org. Lett. 2018; 20: 44
90 Lee S.-C, Liao H.-H, Chatupheeraphat A, Rueping M. Chem. Eur. J. 2018; 24: 3608
91 Liu C, Szostak M. Chem. Commun. 2018; 54: 2130
92 Ishitobi K, Isshiki R, Asahara KK, Lim C, Muto K, Yamaguchi J. Chem. Lett. 2018; 47: 756

93a Cao H, Liu X, Bie F, Shi Y, Han Y, Yan P, Szostak M, Liu C. J. Org. Chem. 2021; 86: 10829
93b Zhou J.-Y, Tian R, Zhu Y.-M. J. Org. Chem. 2021; 86: 12148
93c Cao H, Liu X, Bie F, Shi Y, Han Y, Yan P, Szostak M, Liu C. Org. Chem. Front. 2021; 8: 1587
93d Wang S.-F, Li C.-E, Liu Y.-C, Mallikarjuna Reddy D, Sidick Basha R, Park JK, Lee S, Lee C.-F. Asian J. Org. Chem. 2020; 9: 1826
93e Han M.-L, Chen J.-J, Xu H, Huang Z.-C, Huang W, Liu Y.-W, Wang X, Liu M, Guo Z.-Q, Dai H.-X. JACS Au 2021; 1: 1877

94 Brigham CE, Malapit CA, Lalloo N, Sanford MS. ACS Catal. 2020; 10: 8315
95 Zhou J.-Y, Zhu Y.-M. Eur. J. Org. Chem. 2021; 2021: 2452
96 Zhou J.-Y, Tao S.-W, Liu R.-Q, Zhu Y.-M. J. Org. Chem. 2019; 84: 11891
97 Bie F, Liu X, Cao H, Shi Y, Zhou T, Szostak M, Liu C. Org. Lett. 2021; 23: 8098
98 Liu C, Szostak M. Org. Chem. Front. 2021; 8: 4805
99 Zheng Z.-J, Jiang C, Shao P.-C, Liu W.-F, Zhao T.-T, Xu P.-F, Wei H. Chem. Commun. 2019; 55: 1907
100 Duan Z, Ranjit S, Zhang P, Liu X. Chem. Eur. J. 2009; 15: 3666
101 Becht J.-M, Le Drian C. J. Org. Chem. 2011; 76: 6327
102 Li M, Hoover JM. Chem. Commun. 2016; 52: 8733
103 Green K.-A, Hoover JM. ACS Catal. 2020; 10: 1769
104 Liu M, Zhang Z, Chen B, Meng Q, Zhang P, Song J, Han B. Chem. Sci. 2020; 11: 7634
105 Liu F, Yi W. Org. Chem. Front. 2018; 5: 428

106a Fu Z, Li Z, Xiong Q, Cai H. Eur. J. Org. Chem. 2014; 2014: 7798
106b Hu L, Wang D, Chen X, Yu L, Yu Y, Tan Z, Zhu G. Org. Biomol. Chem. 2017; 15: 5674

107a Exner B, Bayarmagnai B, Jia F, Goossen LJ. Chem. Eur. J. 2015; 21: 17220
107b Exner B, Bayarmagnai B, Matheis C, Goossen LJ. J. Fluorine Chem. 2017; 198: 89

108a Wang R, Chen F, Jiang L, Yi W. Adv. Synth. Catal. 2021; 363: 1904
108b Wang P, Tang S, Huang P, Lei A. Angew. Chem. Int. Ed. 2017; 56: 3009

109 Zhang Y, Sun W, Li C. Synthesis 2022; 54: 281
110 Wang Y, Deng L, Wang X, Wu Z, Wang Y, Pan Y. ACS Catal. 2019; 9: 1630
111 Liu D, Ma HX, Fang P, Mei TS. Angew. Chem. Int. Ed. 2019; 58: 5033
112 Zhu M, Alami M, Messaoudi S. Chem. Commun. 2020; 56: 4464
113 Ang NW. J, Ackermann L. Chem. Eur. J. 2021; 27: 4883
114 Zhang F, Wang Y, Wang Y, Pan Y. Org. Lett. 2021; 23: 7524
115 Kang J.-C, Li Z.-H, Chen C, Dong L.-K, Zhang S.-Y. J. Org. Chem. 2021; 86: 15326
116 Wang Y, Zhang F, Wang Y, Pan Y. Eur. J. Org. Chem. 2022; 2022: e202101462
117 Savarin C, Srogl J, Liebeskind LS. Org. Lett. 2002; 4: 4309
118 Graßl S, Hamze C, Koller TJ, Knochel P. Chem. Eur. J. 2019; 25: 3752
119 Dong Z.-B, Balkenhohl M, Tan E, Knochel P. Org. Lett. 2018; 20: 7581

120a Chowdhury S, Roy S. Tetrahedron Lett. 1997; 38: 2149
120b Taniguchi N. J. Org. Chem. 2004; 69: 6904
120c Taniguchi N, Onami T. J. Org. Chem. 2004; 69: 915
120d Fukuzawa S.-i, Tanihara D, Kikuchi S. Synlett 2006; 2145
120e Gómez-Benítez V, Baldovino-Pantaleón O, Herrera-Álvarez C, Toscano RA, Morales-Morales D. Tetrahedron Lett. 2006; 47: 5059

121a Fang Y, Rogge T, Ackermann L, Wang S.-Y, Ji S.-J. Nat. Commun. 2018; 9: 2240
121b Li J, Rao W, Wang S.-Y, Ji S.-J. J. Org. Chem. 2019; 84: 11542
121c Liu Y, Xing S, Zhang J, Liu W, Xu Y, Zhang Y, Yang K, Yang L, Jiang K, Shao X. Org. Chem. Front. 2022; 9: 1375

122 Zhang W, Huang M, Zou Z, Wu Z, Ni S, Kong L, Zheng Y, Wang Y, Pan Y. Chem. Sci. 2021; 12: 2509
123 Lian Z, Bhawal BN, Yu P, Morandi B. Science 2017; 356: 1059
124 Rivero-Crespo MA, Toupalas G, Morandi B. J. Am. Chem. Soc. 2021; 143: 21331
125 Delcaillau T, Bismuto A, Lian Z, Morandi B. Angew. Chem. Int. Ed. 2020; 59: 2110

126a Delcaillau T, Boehm P, Morandi B. J. Am. Chem. Soc. 2021; 143: 3723
126b Delcaillau T, Morandi B. Chem. Eur. J. 2021; 27: 11823

127 Isshiki R, Kurosawa MB, Muto K, Yamaguchi J. J. Am. Chem. Soc. 2021; 143: 10333

128a Gensch T, James MJ, Dalton T, Glorius F. Angew. Chem. Int. Ed. 2018; 57: 2296
128b Gandeepan P, Muller T, Zell D, Cera G, Warratz S, Ackermann L. Chem. Rev. 2019; 119: 2192
128c Grover N, Senge MO. Synthesis 2020; 52: 3295
128d Lam NY. S, Wu K, Yu JQ. Angew. Chem. Int. Ed. 2021; 60: 15767

129a Liu J, Zheng L. Adv. Synth. Catal. 2019; 361: 1710
129b Iwasaki M, Nishihara Y. Dalton Trans. 2016; 45: 15278
129c Ma W, Kaplaneris N, Fang X, Gu L, Mei R, Ackermann L. Org. Chem. Front. 2020; 7: 1022

130 Yang Y, Hou W, Qin L, Du J, Feng H, Zhou B, Li Y. Chem. Eur. J. 2014; 20: 416
131 Rui X, Zhu Y, Dai R, Huang C, Wang C, Si D, Wang X, Zhang X, Wen H, Li W, Liu J. Asian J. Org. Chem. 2021; 10: 793
132 Shi G, Khan R, Zhang X, Yang Y, Zhan Y, Li J, Luo Y, Fan B. Asian J. Org. Chem. 2020; 9: 788
133 Yang S, Feng B, Yang Y. J. Org. Chem. 2017; 82: 12430
134 Wen J, Wu A, Wang M, Zhu J. J. Org. Chem. 2015; 80: 10457
135 Maity S, Karmakar U, Samanta R. Chem. Commun. 2017; 53: 12197
136 Lin J, Hu L, Chen C, Feng H, Yu Y, Yang Y, Zhou B. Org. Lett. 2021; 23: 1194
137 Liu C, Fang Y, Wang S.-Y, Ji S.-J. Org. Lett. 2018; 20: 6112
138 Liu C, Fang Y, Wang S.-Y, Ji S.-J. ACS Catal. 2019; 9: 8910
139 Sumit, Chandra D, Thakur A, Dhiman AK, Sharma U. J. Org. Chem. 2021; 86: 13754

140a Iwasaki M, Iyanaga M, Tsuchiya Y, Nishimura Y, Li W, Li Z, Nishihara Y. Chem. Eur. J. 2014; 20: 2459
140b Xu C, Shen Q. Org. Lett. 2014; 16: 2046

141 Qiu R, Reddy VP, Iwasaki T, Kambe N. J. Org. Chem. 2015; 80: 367
142 Chaitanya M, Anbarasan P. Org. Lett. 2018; 20: 3362
143 Zhang X.-S, Li G, Zhang X.-G, Zhang X.-H. Tetrahedron 2015; 71: 5458
144 Tzouras NV, Stamatopoulos IK, Papastavrou AT, Liori AA, Vougioukalakis GC. Coord. Chem. Rev. 2017; 343: 25
145 Gao F, Zhu W, Zhang D, Li S, Wang J, Liu H. J. Org. Chem. 2016; 81: 9122
146 Zhu J, Chen Y, Lin F, Wang B, Chen Z, Liu L. Org. Biomol. Chem. 2015; 13: 3711
147 Yan S.-Y, Liu Y.-J, Liu B, Liu Y.-H, Shi B.-F. Chem. Commun. 2015; 51: 4069

148a Lin C, Li D, Wang B, Yao J, Zhang Y. Org. Lett. 2015; 17: 1328
148b Lin C, Yu W, Yao J, Wang B, Liu Z, Zhang Y. Org. Lett. 2015; 17: 1340
148c Ye X, Petersen JL, Shi X. Chem. Commun. 2015; 51: 7863

149 Müller T, Ackermann L. Chem. Eur. J. 2016; 22: 14151

150a Chu L, Yue X, Qing F.-L. Org. Lett. 2010; 12: 1644
150b Chen C, Xu XH, Yang B, Qing FL. Org. Lett. 2014; 16: 3372
150c Zhang X, Zeng W, Yang Y, Huang H, Liang Y. Org. Lett. 2014; 16: 876

151 Xiong Y.-S, Yu Y, Weng J, Lu G. Org. Chem. Front. 2018; 5: 982
152 Yang L.-F, Liu C.-G, Xu X.-P, Ji S.-J. Org. Biomol. Chem. 2016; 14: 2993
153 Tian L.-L, Lu S, Zhang Z.-H, Huang E.-L, Yan H.-T, Zhu X, Hao X.-Q, Song M.-P. J. Org. Chem. 2019; 84: 5213
154 Le Bescont J, Breton-Patient C, Piguel S. Eur. J. Org. Chem. 2020; 2020: 2101
155 Moselage M, Li J, Ackermann L. ACS Catal. 2016; 6: 498

156a Li M, Wang JJ. Org. Lett. 2018; 20: 6490
156b Hu L, Chen X, Yu L, Yu Y, Tan Z, Zhu G, Gui Q. Org. Chem. Front. 2018; 5: 216

157 Gensch T, Klauck FJ. R, Glorius F. Angew. Chem. Int. Ed. 2016; 55: 11287
158 Panova YS, Kashin AS, Vorobev MG, Degtyareva ES, Ananikov VP. ACS Catal. 2016; 6: 3637
159 Liu X.-G, Li Q, Wang H. Adv. Synth. Catal. 2017; 359: 1942
160 López-Resano S, Martínez de Salinas S, Garcés-Pineda FA, Moneo-Corcuera A, Galán-Mascarós JR, Maseras F, Pérez-Temprano MH. Angew. Chem. Int. Ed. 2021; 60: 11217
161 Ghorai J, Kesavan A, Anbarasan P. Chem. Commun. 2021; 57: 10544
162 Qin L, Wu H.-b, Weng L, Shen Q, Chen H. SynOpen 2020; 4: 17
163 Hsu W.-C, Li C.-E, Lee C.-F. Asian J. Org. Chem. 2017; 6: 1667
164 Xiao F, Yuan S, Wang D, Liu S, Huang H, Deng G.-J. Adv. Synth. Catal. 2019; 361: 3331

165a Ma W, Weng Z, Rogge T, Gu L, Lin J, Peng A, Luo X, Gou X, Ackermann L. Adv. Synth. Catal. 2018; 360: 704
165b Bag R, Sarkar T, Kumar SV, Talukdar K, Punniyamurthy T. J. Chem. Sci. 2019; 131: 115

166a Posner T. Ber. Dtsch. Chem. Ges. 1905; 38: 646
166b Bader H, Cross LC, Heilbron I, Jones ER. H. J. Chem. Soc. 1949; 619

167a Crossley SW. M, Obradors C, Martinez RM, Shenvi RA. Chem. Rev. 2016; 116: 8912
167b Castarlenas R, Di Giuseppe A, Perez-Torrente JJ, Oro LA. Angew. Chem. Int. Ed. 2013; 52: 211
167c Beletskaya IP, Nájera C, Yus M. Russ. Chem. Rev. 2021; 90: 70

168a Cao C, Fraser LR, Love JA. J. Am. Chem. Soc. 2005; 127: 17614
168b Di Giuseppe A, Castarlenas R, Pérez-Torrente JJ, Crucianelli M, Polo V, Sancho R, Lahoz FJ, Oro LA. J. Am. Chem. Soc. 2012; 134: 8171
168c Ogawa A, Ikeda T, Kimura K, Hirao T. J. Am. Chem. Soc. 1999; 121: 5108

169 Kiemele ER, Wathier M, Bichler P, Love JA. Org. Lett. 2016; 18: 492
170 Strydom I, Guisado-Barrios G, Fernandez I, Liles DC, Peris E, Bezuidenhout DI. Chem. Eur. J. 2017; 23: 1393
171 Tolley LC, Fernández I, Bezuidenhout DI, Guisado-Barrios G. Catal. Sci. Technol. 2021; 11: 516
172 Kleinhans G, Guisado-Barrios G, Liles DC, Bertrand G, Bezuidenhout DI. Chem. Commun. 2016; 52: 3504
173 Pritzius AB, Breit B. Angew. Chem. Int. Ed. 2015; 54: 3121
174 Pritzius AB, Breit B. Angew. Chem. Int. Ed. 2015; 54: 15818
175 Kennemur JL, Kortman GD, Hull KL. J. Am. Chem. Soc. 2016; 138: 11914
176 Han L, Li Y, Liu T. Dalton Trans. 2018; 47: 150
177 Yang X.-H, Davison RT, Dong VM. J. Am. Chem. Soc. 2018; 140: 10443
178 Yang X.-H, Davison RT, Nie S.-Z, Cruz FA, McGinnis TM, Dong VM. J. Am. Chem. Soc. 2019; 141: 3006
179 Wen X, Zhou X, Li W, Du C, Ke Z, Zhao C. ACS Catal. 2021; 11: 7659
180 Nie S, Lu A, Kuker EL, Dong VM. J. Am. Chem. Soc. 2021; 143: 6176

181a Corma A, González-Arellano C, Iglesias M, Sánchez F. Appl. Catal., A 2010; 375: 49
181b Biswas S, Samec JS. M. Chem. Commun. 2012; 48: 6586
181c Mudd RJ, Young PC, Jordan-Hore JA, Rosair GM, Lee A.-L. J. Org. Chem. 2012; 77: 7633
181d Biswas S, Dahlstrand C, Watile RA, Kalek M, Himo F, Samec JS. M. Chem. Eur. J. 2013; 19: 17939

182 Martínez-Lara F, Suárez A, Velasco N, Suárez-Pantiga S, Sanz R. Adv. Synth. Catal. 2022; 364: 132
183 Tamai T, Fujiwara K, Higashimae S, Nomoto A, Ogawa A. Org. Lett. 2016; 18: 2114
184 Kristensen SK, Laursen SL. R, Taarning E, Skrydstrup T. Angew. Chem. Int. Ed. 2018; 57: 13887
185 Kuniyasu H, Ogawa A, Sato K, Ryu I, Kambe N, Sonoda N. J. Am. Chem. Soc. 1992; 114: 5902

186a Ananikov VP, Orlov NV, Zalesskiy SS, Beletskaya IP, Khrustalev VN, Morokuma K, Musaev DG. J. Am. Chem. Soc. 2012; 134: 6637
186b Gerber R, Frech CM. Chem. Eur. J. 2012; 18: 8901
186c Degtyareva ES, Burykina JV, Fakhrutdinov AN, Gordeev EG, Khrustalev VN, Ananikov VP. ACS Catal. 2015; 5: 7208

187 Sahharova LT, Gordeev EG, Eremin DB, Ananikov VP. ACS Catal. 2020; 10: 9872
188 Lopes AB, Choury M, Wagner P, Gulea M. Org. Lett. 2019; 21: 5943
189 Ogawa A, Kawakami J.-i, Sonoda N, Hirao T. J. Org. Chem. 1996; 61: 4161
190 Tamai T, Ogawa A. J. Org. Chem. 2014; 79: 5028
191 Kathe PM, Fleischer I. Org. Lett. 2019; 21: 2213
192 Zhang Y, Xu X, Zhu S. Nat. Commun. 2019; 10: 1752

193a Ananikov VP, Orlov NV, Beletskaya IP. Organometallics 2006; 25: 1970
193b Malyshev DA, Scott NM, Marion N, Stevens ED, Ananikov VP, Beletskaya IP, Nolan SP. Organometallics 2006; 25: 4462
193c Ananikov VP, Gayduk KA, Orlov NV, Beletskaya IP, Khrustalev VN, Antipin MY. Chem. Eur. J. 2010; 16: 2063

194 Ren S, Xue B, Zheng T, Wang Y, Sun H, Li X, Fuhr O, Fenske D. Appl. Organomet. Chem. 2020; 34: e5291

195a Nurhanna Riduan S, Ying JY, Zhang Y. Org. Lett. 2012; 14: 1780
195b Trostyanskaya IG, Beletskaya IP. Synlett 2012; 535
195c Watile RA, Biswas S, Samec JS. M. Green Chem. 2013; 15: 3176

196 Wang G, Khan R, Liu H, Shen G, Yang F, Chen J, Zhou Y, Fan B. Organometallics 2020; 39: 2037

197a Sonehara T, Murakami S, Yamazaki S, Kawatsura M. Org. Lett. 2017; 19: 4299
197b Yang T, Lu L, Shen Q. Chem. Commun. 2015; 51: 5479
197c Cabrero-Antonino JR, Leyva-Pérez A, Corma A. Adv. Synth. Catal. 2012; 354: 678

198 Taniguchi N. J. Org. Chem. 2020; 85: 6528

199a Kucinski K, Pawluc P, Marciniec B, Hreczycho G. Chem. Eur. J. 2015; 21: 4940
199b Kuciński K, Pawluć P, Hreczycho G. Adv. Synth. Catal. 2015; 357: 3936

200a Lou J, Wang Q, Wu P, Wang H, Zhou Y.-G, Yu Z. Chem. Soc. Rev. 2020; 49: 4307
200b Wang L, He W, Yu Z. Chem. Soc. Rev. 2013; 42: 599

201a Hooper JF, Chaplin AB, González-Rodríguez C, Thompson AL, Weller AS, Willis MC. J. Am. Chem. Soc. 2012; 134: 2906
201b Arisawa M, Igarashi Y, Tagami Y, Yamaguchi M, Kabuto C. Tetrahedron Lett. 2011; 52: 920
201c Arambasic M, Hooper JF, Willis MC. Org. Lett. 2013; 15: 5162

202a Iwasaki M, Fujino D, Wada T, Kondoh A, Yorimitsu H, Oshima K. Chem. Asian J. 2011; 6: 3190
202b Hua R, Takeda H, Onozawa S.-y, Abe Y, Tanaka M. J. Am. Chem. Soc. 2001; 123: 2899
202c Minami Y, Kuniyasu H, Sanagawa A, Kambe N. Org. Lett. 2010; 12: 3744
202d Minami Y, Kuniyasu H, Miyafuji K, Kambe N. Chem. Commun. 2009; 3080
202e Toyofuku M, Fujiwara S.-i, Shin-ike T, Kuniyasu H, Kambe N. J. Am. Chem. Soc. 2005; 127: 9706

203a Sugoh K, Kuniyasu H, Sugae T, Ohtaka A, Takai Y, Tanaka A, Machino C, Kambe N, Kurosawa H. J. Am. Chem. Soc. 2001; 123: 5108
203b Toyofuku M, Fujiwara S.-i, Shin-ike T, Kuniyasu H, Kambe N. J. Am. Chem. Soc. 2008; 130: 10504

204 Ren P, Pike SD, Pernik I, Weller AS, Willis MC. Organometallics 2015; 34: 711
205 Shibata T, Mitake A, Akiyama Y, Kanyiva KS. Chem. Commun. 2017; 53: 9016
206 Iwasaki M, Topolovčan N, Hu H, Nishimura Y, Gagnot G, Na nakorn R, Yuvacharaskul R, Nakajima K, Nishihara Y. Org. Lett. 2016; 18: 1642
207 Uno D, Nogi K, Yorimitsu H. Org. Lett. 2019; 21: 8295
208 Wu J, Xu W.-H, Lu H, Xu P.-F. Adv. Synth. Catal. 2021; 363: 3013
209 Hosoya Y, Kobayashi I, Mizoguchi K, Nakada M. Org. Lett. 2019; 21: 8280
210 Kim H, Jang J, Shin S. J. Am. Chem. Soc. 2020; 142: 20788
211 Wang J, Zhang S, Xu C, Wojtas L, Akhmedov NG, Chen H, Shi X. Angew. Chem. Int. Ed. 2018; 57: 6915

212a Inami T, Kurahashi T, Matsubara S. Chem. Commun. 2011; 47: 9711
212b Inami T, Baba Y, Kurahashi T, Matsubara S. Org. Lett. 2011; 13: 1912
212c Hua R, Takeda H, Onozawa S.-y, Abe Y, Tanaka M. Org. Lett. 2007; 9: 263

213 Inami T, Kurahashi T, Matsubara S. Chem. Commun. 2015; 51: 1285
214 Liu W, Xu W, Wang J, Lu H, Xu P.-F, Wei H. Chem. Eur. J. 2021; 27: 7651
215 Shibata T, Sekine A, Akino M, Ito M. Chem. Commun. 2021; 57: 9048
216 Inami T, Takahashi T, Kurahashi T, Matsubara S. J. Am. Chem. Soc. 2019; 141: 12541
217 Miura T, Fujimoto Y, Funakoshi Y, Murakami M. Angew. Chem. Int. Ed. 2015; 54: 9967
218 Dairo TO, Woo LK. Organometallics 2017; 36: 927
219 Zheng R.-H, Guo H.-C, Chen T.-T, Huang Q, Huang G.-B, Jiang H.-J. RSC Adv. 2018; 8: 25123
220 Urriolabeitia EP, Ruiz S. Org. Biomol. Chem. 2019; 17: 2542
221 Kamiya I, Kawakami J.-i, Yano S, Nomoto A, Ogawa A. Organometallics 2006; 25: 3562
222 Pawliczek M, Garve LK. B, Werz DB. Org. Lett. 2015; 17: 1716
223 Bürger M, Loch MN, Jones PG, Werz DB. Chem. Sci. 2020; 11: 1912
224 Higashimae S, Kurata D, Kawaguchi S.-i, Kodama S, Sonoda M, Nomoto A, Ogawa A. J. Org. Chem. 2018; 83: 5267
225 Vahabi AH, Alizadeh A, Khavasi HR, Bazgir A. Eur. J. Org. Chem. 2017; 2017: 5347
226 Masuya Y, Tobisu M, Chatani N. Org. Lett. 2016; 18: 4312
227 Li J, Li C, Ouyang L, Li C, Yang S, Wu W, Jiang H. Adv. Synth. Catal. 2018; 360: 1138
228 Ishitobi K, Muto K, Yamaguchi J. ACS Catal. 2019; 9: 11685
229 Gómez JE, Guo W, Kleij AW. Org. Lett. 2016; 18: 6042
230 Shen X.-Q, Wang S.-Q, Fan D, Zhang X.-G, Tu H.-Y. J. Org. Chem. 2021; 86: 1591
231 Wang Y, Deng J, Chen J, Cao F, Hou Y, Yang Y, Deng X, Yang J, Wu L, Shao X, Shi T, Wang Z. ACS Catal. 2020; 10: 2707
232 Zhou Y, Wang Y, Lou Y, Song Q. Chem. Commun. 2019; 55: 10265
233 Gao Y, Gao Y, Tang X, Peng J, Hu M, Wu W, Jiang H. Org. Lett. 2016; 18: 1158