Transition-Metal-Catalyzed Cross-Coupling Reactions of Grignard Reagents

Kinga Juhász; Ágnes Magyar; Zoltán Hell

doi:10.1055/s-0040-1705986

Synthesis, Table of Contents

Synthesis 2021; 53(06): 983-1002
DOI: 10.1055/s-0040-1705986

review

Transition-Metal-Catalyzed Cross-Coupling Reactions of Grignard Reagents

Kinga Juhász

,

Ágnes Magyar

,

Zoltán Hell∗

Abstract

All articles of this category

Abstract

Transition-metal-catalyzed cross-coupling of organohalides, ethers, sulfides, amines, and alcohols (and derivatives thereof) with Grignard reagents, known as the Kumada–Tamao–Corriu reaction, can be used to prepare important intermediates in the synthesis of numerous biologically active compounds. The most frequently used transition metals are nickel, palladium, and iron, but there are several examples for cross-coupling reactions catalyzed by copper, cobalt, manganese, chromium, etc. salts and complexes. The aim of this review is to summarize the most important transition-metal-catalyzed cross-coupling reactions realized in the period 2000 to 2020.

1 Introduction

2 Nickel Catalysis

3 Palladium Catalysis

4 Iron Catalysis

5 Catalysis by Other Transition Metals

5.1 Cobalt Catalysis

5.2 Copper Catalysis

5.3 Manganese Catalysis

5.4 Chromium Catalysis

6 Conclusion

Key words

transition metals - Grignard reagent - cross-coupling - organometallic reagent - organic halides - Kumada–Tamao–Corriu coupling

Full Text

References

References
1 Barbier P. C. R. Hebd. Seances Acad. Sci. 1899; 128: 110
2 Grignard V. C. R. Hebd. Seances Acad. Sci. 1900; 130: 1322
3 Tamao K, Sumitani K, Kumada M. J. Am. Chem. Soc. 1972; 94: 4374
4 Corriu RJ. P, Masse JP. J. Chem. Soc., Chem. Commun. 1972; 144a
5 Kharash MS, Fields EK. J. Am. Chem. Soc. 1941; 63: 2316
6 Okamura H, Miura M, Takei H. Tetrahedron Lett. 1979; 20: 43
7 Guérinot A, Cossy J. Acc. Chem. Res. 2020; 53: 1351
8 Gandeepan P, Muller T, Zell D, Cera G, Warratz S, Ackermann L. Chem. Rev. 2019; 119: 2192
9 Cheng LJ, Mankad NP. Chem. Soc. Rev. 2020; 49: 8036
10 Piontek A, Bisz E, Szostak M. Angew. Chem. Int. Ed. 2018; 57: 11116
11 Liang L.-C, Chien P.-S, Lin J.-M, Huang M.-H, Huang Y.-L, Liao J.-H. Organometallics 2006; 25: 1399
12 Wang Z.-X, Wang L. Chem. Commun. 2007; 2423
13 Sun K, Wang L, Wang Z.-X. Organometallics 2008; 27: 5649
14 Vechorkin O, Csok Z, Scopelliti R, Hu X. Chem. Eur. J. 2009; 15: 3889
15 Vechorkin O, Godinat A, Scopelliti R, Hu X. Angew. Chem. Int. Ed. 2011; 50: 11777
16 Terao J, Watanabe H, Ikumi A, Kuniyasu H, Kambe N. J. Am. Chem. Soc. 2002; 124: 4222
17 Terao J, Kambe N. Bull. Chem. Soc. Jpn. 2006; 79: 663
18 Terao J, Ikumi A, Kuniyasu H, Kambe N. J. Am. Chem. Soc. 2003; 125: 5646
19 Terao J, Todo H, Watanabe H, Ikumi A, Kambe N. Angew. Chem. Int. Ed. 2004; 43: 6180
20 Chiang C.-C, Luh T.-Y. Synlett 2001; 977
21 Wenkert E, Michelotti EL, Swindell CS. J. Am. Chem. Soc. 1979; 101: 2246
22 Wenkert E, Michelotti EL, Swindell CS, Tingoli M. J. Org. Chem. 1984; 49: 4894
23 Dankwardt JW. Angew. Chem. Int. Ed. 2004; 43: 2428
24 Wolf J, Labande A, Natella M, Daran J.-C, Poli R. J. Mol. Catal. A: Chem. 2006; 259: 205
25 Guan B.-T, Xiang S.-K, Wang B.-Q, Sun Z.-P, Wang Y, Zhao K.-Q, Shi Z.-J. J. Am. Chem. Soc. 2008; 130: 3268
26 Guan B.-T, Xiang S.-K, Wu T, Sun Z.-P, Wang B.-Q, Zhao K.-Q, Shi Z.-J. Chem. Commun. 2008; 1437
27 Kanemura S, Kondoh A, Yorimitsu H, Oshima K. Synthesis 2008; 2659
28 Vechorkin O, Hu X. Angew. Chem. Int. Ed. 2009; 48: 2937
29 Monnereau L, Sémeril D, Matt D, Toupet L, Mota AJ. Adv. Synth. Catal. 2009; 351: 1383
30 Yu D.-G, Li B.-J, Zheng S.-F, Guan B.-T, Wang B.-Q, Shi Z.-J. Angew. Chem. Int. Ed. 2010; 49: 4566
31 Xie L.-G, Wang Z.-X. Chem. Eur. J. 2011; 17: 4972
32 Zhao F, Yu D.-G, Zhu R.-Y, Xi Z, Shi Z.-J. Chem. Lett. 2011; 40: 1001
33 Iglesias MJ, Prieto A, Nicasio MC. Org. Lett. 2012; 14: 4318
34 Onoabedje EA, Ezema BE, Ezema CG, Ugwu DI. Chem. Process Eng. Res. 2013; 8: 6
35 Xue F, Zhao J, Hor TS. A. Chem. Commun. 2013; 49: 10121
36 Yang Z, Chen X, Kong W, Xia S, Zheng R, Luo F, Zhu G. Org. Biomol. Chem. 2013; 11: 2175
37 Xue F, Zhao J, Hor TS, Hayashi T. J. Am. Chem. Soc. 2015; 137: 3189
38 Tobisu M, Takahira T, Chatani N. Org. Lett. 2015; 17: 4352
39 Tobisu M, Takahira T, Morioka T, Chatani N. J. Am. Chem. Soc. 2016; 138: 6711
40 Harkness GJ, Clarke ML. Catal. Sci. Technol. 2018; 8: 328
41 O’Neill MJ, Riesebeck T, Cornella J. Angew. Chem. Int. Ed. 2018; 57: 9103
42 Wu Z, Si T, Xu G, Xu B, Tang W. Chin. Chem. Lett. 2019; 30: 597
43 Piontek A, Ochędzan-Siodłak W, Bisz E, Szostak M. Adv. Synth. Catal. 2019; 361: 2329
44 He X.-Y, Zhang Z.-X, Li C.-J, Li Y. Russ. J. Gen. Chem. 2020; 89: 2591
45 Zhang ZB, Ji CL, Yang C, Chen J, Hong X, Xia JB. Org. Lett. 2019; 21: 1226
46 Yang B, Wang ZX. J. Org. Chem. 2020; 85: 4772
47 Muller V, Ghorai D, Capdevila L, Messinis AM, Ribas X, Ackermann L. Org. Lett. 2020; 22: 7034
48 Zhang Y, Chen Y, Zhang Z, Liu S, Shen X. Org. Lett. 2020; 22: 970
49 Dawson DD, Oswald VF, Borovik AS, Jarvo ER. Chem. Eur. J. 2020; 26: 3044
50 Yamamura M, Moritani I, Murahashi S.-I. J. Organomet. Chem. 1975; 91: C39
51 Cassar L. J. Organomet. Chem. 1975; 93: 253
52 Knappke CE, Jacobi von Wangelin A. Chem. Soc. Rev. 2011; 40: 4948
53 Rottländer M, Boymond L, Bérillon L, Leprêtre A, Varchi G, Avolio S, Laaziri H, Quéguiner G, Ricci A, Cahiez G, Knochel P. Chem. Eur. J. 2000; 6: 767
54 Trécourt F, Breton G, Bonnet V, Mongin F, Marsais F, Quéguiner G. Tetrahedron Lett. 1999; 40: 4339
55 Trécourt F, Breton G, Bonnet V, Mongin F, Marsais F, Quéguiner G. Tetrahedron 2000; 56: 1349
56 Bolm C, Pupowicz D. Tetrahedron Lett. 1997; 38: 7349
57 Bonnet V, Mongin F, Trécourt F, Quéguiner G, Knochel P. Tetrahedron 2002; 58: 4429
58 Frisch AC, Shaikh N, Zapf A, Beller M. Angew. Chem. Int. Ed. 2002; 41: 4056
59 Kirchhoff JH, Dai C, Fu GC. Angew. Chem. Int. Ed. 2002; 41: 1945
60 Terao J, Naitoh Y, Kuniyasu H, Kambe N. Chem. Lett. 2003; 32: 890
61 Terao J, Naitoh Y, Kuniyasu H, Kambe N. Chem. Commun. 2007; 825
62 Huang K, Nolan SP. J. Am. Chem. Soc. 1999; 121: 9889
63 Frisch AC, Zapf A, Briel O, Kayser B, Shaikh N, Beller M. J. Mol. Catal. A: Chem. 2004; 214: 231
64 Hartmann CE, Nolan SP, Cazin CS. J. Organometallics 2009; 28: 2915
65 Itami K, Mineno M, Muraoka N, Yoshida J. J. Am. Chem. Soc. 2004; 126: 11778
66 Ackermann L, Gschrei CJ, Althammer A, Riederer M. Chem. Commun. 2006; 1419
67 Hills ID, Netherton MR, Fu GC. Angew. Chem. Int. Ed. 2003; 42: 5749
68 Rodríguez N, Ramírez de Arellano C, Asensio G, Medio-Simón M. Chem. Eur. J. 2007; 13: 4223
69 Altenhoff G, Würtz S, Glorius F. Tetrahedron Lett. 2006; 47: 2925
70 Rudolph A, Rackelmann N, Lautens M. Angew. Chem. Int. Ed. 2007; 46: 1485
71 Martin R, Buchwald SL. J. Am. Chem. Soc. 2007; 129: 3844
72 Wolf C, Xu H. J. Org. Chem. 2008; 73: 162
73 Li GY. J. Organomet. Chem. 2002; 653: 63
74 López-Pérez A, Adrio J, Carretero JC. Org. Lett. 2009; 11: 5514
75 Wenkert E, Han A.-L, Jenny C.-J. J. Chem. Soc., Chem. Commun. 1988; 975
76 Reeves JT, Fandrick DR, Tan Z, Song JJ, Lee H, Yee NK, Senanyake CH. Org. Lett. 2010; 12: 4388
77 Ackermann L, Kapdi AR, Fenner S, Kornhaass C, Schulzke C. Chem. Eur. J. 2011; 17: 2965
78 Sugita N, Hayashi S, Hino F, Takanami T. J. Org. Chem. 2012; 77: 10488
79 Dai W, Xiao J, Jin G, Wu J, Cao S. J. Org. Chem. 2014; 79: 10537
80 Krasovskiy AL, Haley S, Voigtritter K, Lipshutz BH. Org. Lett. 2014; 16: 4066
81 Jeanne-Julien L, Astier E, Lai-Kuen R, Genta-Jouve G, Roulland E. Org. Lett. 2018; 20: 1430
82 Jeanne-Julien L, Masson G, Astier E, Genta-Jouve G, Servajean V, Beau JM, Norsikian S, Roulland E. Org. Lett. 2017; 19: 4006
83 Chen Z, So CM. Org. Lett. 2020; 22: 3879
84 Wu C, McCollom SP, Zheng Z, Zhang J, Sha S.-C, Li M, Walsh PJ, Tomson NC. ACS Catal. 2020; 10: 7934
85 Gilman H, Lichtenwalter M. J. Am. Chem. Soc. 1939; 61: 957
86 Tamura M, Kochi J. J. Am. Chem. Soc. 1971; 93: 1487
87 Tamura M, Kochi J. Synthesis 1971; 303
88 Neumann SM, Kochi JK. J. Org. Chem. 1975; 40: 599
89 Smith RS, Kochi JK. J. Org. Chem. 1976; 41: 502
90 Kochi JK. Acc. Chem. Res. 1974; 7: 351

91a Negishi E.-I, Baba S. J. Chem. Soc., Chem. Commun. 1976; 596b
91b Baba S, Negishi E. J. Am. Chem. Soc. 1976; 98: 6729
91c Negishi E, King AO, Okukado N. J. Org. Chem. 1977; 42: 1821
91d Negishi E, Van Horn DE. J. Am. Chem. Soc. 1977; 99: 3168

92 Bogdanović B, Schwickardi M. Angew. Chem. Int. Ed. 2000; 39: 4610
93 Fürstner A, Leitner A. Angew. Chem. Int. Ed. 2002; 41: 609
94 Martin R, Fürstner A. Angew. Chem. Int. Ed. 2004; 43: 3955
95 Scheiper B, Bonnekessel M, Krause H, Fürstner A. J. Org. Chem. 2004; 69: 3943
96 Nagano T, Hayashi T. Org. Lett. 2004; 6: 1297
97 Nakamura M, Matsuo K, Ito S, Nakamura E. J. Am. Chem. Soc. 2004; 126: 3686
98 Bedford RB, Bruce DW, Frost RM, Hird M. Chem. Commun. 2005; 4161
99 Bedford RB, Betham M, Bruce DW, Danopoulos AA, Frost RM, Hird M. J. Org. Chem. 2006; 71: 1104
100 Nagano T, Hayashi T. Org. Lett. 2005; 7: 491
101 Cahiez G, Chaboche C, Mahuteau-Betzer F, Ahr M. Org. Lett. 2005; 7: 1943
102 Itami K, Higashi S, Mineno M, Yoshida J. Org. Lett. 2005; 7: 1219
103 Ottesen LK, Ek F, Olsson R. Org. Lett. 2006; 8: 1771
104 Cahiez G, Habiak V, Duplais C, Moyeux A. Angew. Chem. Int. Ed. 2007; 46: 4364
105 Guerinot A, Reymond S, Cossy J. Angew. Chem. Int. Ed. 2007; 46: 6521
106 Cahiez G, Duplais C, Moyeux A. Org. Lett. 2007; 9: 3253
107 Mayer M, Czaplik WM, Jacobi von Wangelin A. Adv. Synth. Catal. 2010; 352: 2147

108a Norinder J, Matsumoto A, Yoshikai N, Nakamura E. J. Am. Chem. Soc. 2008; 130: 5858
108b Yoshikai N, Matsumoto A, Norinder J, Nakamura E. Angew. Chem. Int. Ed. 2009; 48: 2925
108c Nakamura E, Yoshikai N, Matsumoto A, Norinder J. Synlett 2010; 313

109 Yoshikai N, Asako S, Yamakawa T, Ilies L, Nakamura E. Chem. Asian J. 2011; 6: 3059
110 Mo Z, Zhang Q, Deng L. Organometallics 2012; 31: 6518
111 Sun C.-L, Krause H, Fürstner A. Adv. Synth. Catal. 2014; 356: 1281
112 Xing T, Zhang Z, Da Y.-X, Quan Z.-J, Wang X.-C. Asian J. Org. Chem. 2015; 4: 538
113 Gartner D, Stein AL, Grupe S, Arp J, Jacobi von Wangelin A. Angew. Chem. Int. Ed. 2015; 54: 10545
114 Chen X, Quan Z.-J, Wang X.-C. Appl. Organomet. Chem. 2015; 29: 296
115 Liu KM, Liao LY, Duan XF. Chem. Commun. 2015; 51: 1124
116 Kim JG, Son YH, Seo JW, Kang EJ. Eur. J. Org. Chem. 2015; 2015: 1781
117 Shakhmaev RN, Sunagatullina AS, Zorin VV. Russ. J. Org. Chem. 2015; 51: 95
118 Buono FG, Zhang Y, Tan Z, Brusoe A, Yang B.-S, Lorenz JC, Giovannini R, Song JJ, Yee NK, Senanayake CH. Eur. J. Org. Chem. 2016; 2016: 2599
119 Li Z, Liu L, Sun HM, Shen Q, Zhang Y. Dalton Trans. 2016; 45: 17739
120 Piontek A, Szostak M. Eur. J. Org. Chem. 2017; 2017: 7271
121 Seto C, Otsuka T, Takeuchi Y, Tabuchi D, Nagano T. Synlett 2018; 29: 1211
122 Ma E, Jiang Y, Chen Y, Qi L, Yan X, Li Z. Asian J. Org. Chem. 2018; 7: 914
123 Bisz E, Szostak M. J. Org. Chem. 2019; 84: 1640
124 Motohashi H, Kato M, Mikami K. J. Org. Chem. 2019; 84: 6483
125 Wei X.-J, Abdiaj I, Sambiagio C, Li C, Zysman-Colman E, Alcázar J, Noël T. Angew. Chem. Int. Ed. 2019; 58: 13030
126 Deng Y, Wei XJ, Wang X, Sun Y, Noël T. Chem. Eur. J. 2019; 25: 14532
127 Nugent J, Shire BR, Caputo DF. J, Pickford HD, Nightingale F, Houlsby IT. T, Mousseau JJ, Anderson EA. Angew. Chem. Int. Ed. 2020; 59: 11866
128 Bisz E, Szostak M. Molecules 2020; 25: 230
129 Manjón-Mata I, Quirós MT, Buñuel E, Cárdenas DJ. Adv. Synth. Catal. 2020; 362: 146
130 Wei YM, Ma XD, Wang L, Duan XF. Chem. Commun. 2020; 56: 1101
131 Machitani K, Tanaka Y, Nishiyama Y, Fujii A, Saito A, Mori H. J. Flow Chem. 2020; 10: 491
132 Tsuji T, Yorimitsu H, Oshima K. Angew. Chem. Int. Ed. 2002; 41: 4137
133 Ohmiya H, Tsuji T, Yorimitsu H, Oshima K. Chem. Eur. J. 2004; 10: 5640
134 Ohmiya H, Wakabayashi K, Yorimitsu H, Oshima K. Tetrahedron 2006; 62: 2207
135 Cahiez G, Chaboche C, Duplais C, Giulliani A, Moyeux A. Adv. Synth. Catal. 2008; 350: 1484
136 Cahiez G, Chaboche C, Duplais C, Moyeux A. Org. Lett. 2009; 11: 277
137 Ohmiya H, Yorimitsu H, Oshima K. Chem. Lett. 2004; 33: 1240
138 Shirakawa E, Sato T, Imazaki Y, Kimura T, Hayashi T. Chem. Commun. 2007; 4513
139 Li B, Wu Z.-H, Gu Y.-F, Sun C.-L, Wang B.-Q, Shi Z.-J. Angew. Chem. Int. Ed. 2011; 50: 1109
140 Chen Q, Ilies L, Yoshikai N, Nakamura E. Org. Lett. 2011; 13: 3232
141 Iwasaki T, Takagawa H, Singh SP, Kuniyasu H, Kambe N. J. Am. Chem. Soc. 2013; 135: 9604
142 Kambe N, Iwasaki T, Takagawa H, Okamoto K, Singh S, Kuniyasu H. Synthesis 2014; 46: 1583
143 Zhou Y, Wang L, Yuan G, Liu S, Sun X, Yuan C, Yang Y, Bian Q, Wang M, Zhong J. Org. Lett. 2020; 22: 4532
144 Gonnard L, Guerinot A, Cossy J. Chem. Eur. J. 2015; 21: 12797
145 Cahiez G, Chaboche C, Jézéquel M. Tetrahedron 2000; 56: 2733
146 Kofink CC, Knochel P. Org. Lett. 2006; 8: 4121
147 Hintermann L, Xiao L, Labonne A. Angew. Chem. Int. Ed. 2008; 47: 8246
148 Ren P, Stern LA, Hu X. Angew. Chem. Int. Ed. 2012; 51: 9110
149 Terao J, Todo H, Begum SA, Kuniyasu H, Kambe N. Angew. Chem. Int. Ed. 2007; 46: 2086
150 Shen R, Iwasaki T, Terao J, Kambe N. Chem. Commun. 2012; 48: 9313
151 Yang CT, Zhang ZQ, Liang J, Liu JH, Lu XY, Chen HH, Liu L. J. Am. Chem. Soc. 2012; 134: 11124
152 Cahiez G, Gager O, Buendia J. Angew. Chem. Int. Ed. 2010; 49: 1278
153 Dai W, Shi H, Zhao X, Cao S. Org. Lett. 2016; 18: 4284
154 Zhu Y, Xiong T, Han W, Shi Y. Org. Lett. 2014; 16: 6144
155 Kim JH, Chung YK. Chem. Commun. 2013; 49: 11101
156 Kakiya H, Inoue R, Shinokubo H, Oshima K. Tetrahedron 2000; 56: 2131
157 Cahiez G, Lepifre F, Ramiandrasoa P. Synthesis 1999; 2138
158 Cahiez G, Luart D, Lecomte F. Org. Lett. 2004; 6: 4395
159 Rueping M, Ieawsuwan W. Synlett 2007; 247
160 Matson E, Petel B, Purak M. Synlett 2018; 29: 1700
161 Cahiez G, Duplais C, Buendia J. Angew. Chem. Int. Ed. 2009; 48: 6731
162 Ghaleshahi HG, Antonacci G, Madsen R. Eur. J. Org. Chem. 2017; 2017: 1331
163 Antonacci G, Ahlburg A, Fristrup P, Norrby P.-O, Madsen R. Eur. J. Org. Chem. 2017; 2017: 4758
164 Murakami K, Ohmiya H, Yorimitsu H, Oshima K. Org. Lett. 2007; 9: 1569
165 Steib AK, Kuzmina OM, Fernandez S, Flubacher D, Knochel P. J. Am. Chem. Soc. 2013; 135: 15346
166 Kuzmina OM, Knochel P. Org. Lett. 2014; 16: 5208
167 Steib AK, Kuzmina OM, Fernandez S, Malhotra S, Knochel P. Chem. Eur. J. 2015; 21: 1961
168 Bellan AB, Kuzmina OM, Vetsova VA, Knochel P. Synthesis 2017; 49: 188
169 Li J, Ren Q, Cheng X, Karaghiosoff K, Knochel P. J. Am. Chem. Soc. 2019; 141: 18127