Recent Progress in Utilization of Functionalized Organometallic Reagents in Cross Coupling Reactions and Nucleophilic Additions

Jin-Quan Chen; Zhi-Bing Dong

doi:10.1055/s-0040-1706550

Synthesis, Inhaltsverzeichnis

Synthesis 2020; 52(24): 3714-3734
DOI: 10.1055/s-0040-1706550

short review

Recent Progress in Utilization of Functionalized Organometallic Reagents in Cross Coupling Reactions and Nucleophilic Additions

Autoren

Jin-Quan Chen

^aSchool of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430205, P. R. of China eMail: dzb04982@wit.edu.cn
Zhi-Bing Dong∗

^aSchool of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430205, P. R. of China eMail: dzb04982@wit.edu.cn

^bKey Laboratory of Green Chemical Process, Ministry of Education, Wuhan Institute of Technology, Wuhan 430205, P. R. of China

^cMinistry-of-Education Key Laboratory for the Synthesis and Application of Organic Functional Molecules, Hubei University, Wuhan 430062, P. R. of China

^dHubei Key Laboratory of Novel Reactor and Green Chemistry Technology, Wuhan Institute of Technology, Wuhan 430205, P. R. of China

Abstract

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Dedicated to Prof. Dr. Paul Knochel for his tremendous contribution to the development of novel organometallic reagents.

Abstract

Organometallic compounds have become increasingly important in organic synthesis because of their high chemoselectivity and excellent reactivity. Recently, a variety of organometallic reagents were found to facilitate transition-metal-catalyzed cross-coupling reactions and nucleophilic addition reactions. Here, we have summarized the latest progress in cross-coupling reactions and in nucleophilic addition reactions with functionalized organometallic reagents present to illustrate their application value. Due to the tremendous contribution made by the Knochel group towards the development of novel organometallic reagents, this review draws extensively from their work in this area in recent years.

Introduction

1 Transition-Metal-Catalyzed Cross Couplings Involving Organozinc Reagents

2 Transition-Metal-Catalyzed Cross Couplings Involving Organomagnesium Reagents

3 Transition-Metal-Free Cross Couplings Involving Zn and Mg Organometallic Reagents

4 Nucleophilic Additions Involving Zn and Mg Organometallic Reagents

5 Cross-Coupling Reactions or Nucleophilic Additions Involving Mn, Al-, La-, Li-, Sm- and In-Organometallics

6 Conclusion

Key words

organometallic reagent - cross coupling - nucleophilic addition - transition-metal catalyst - synthesis

Volltext

Referenzen

References

1a Balkenhohl M, Knochel P. Chem. Eur. J. 2020; 26: 3688
1b Robertson SD, Uzelac M, Mulvey RE. Chem. Rev. 2019; 119: 8332
1c Mongin F, Harrison-Marchand A. Chem. Rev. 2013; 113: 7563
1d Knochel P, Thaler T, Diene C. Isr. J. Chem. 2010; 50: 547
1e Haag B, Mosrin M, Ila H, Malakhov V, Knochel P. Angew. Chem. Int. Ed. 2011; 50: 9794
1f Dagousset G, Francois C, Leon T, Blanc R, Sansiaume-Dagousset E, Knochel P. Synthesis 2014; 46: 3133
1g Manolikakes SM, Barl NM, Samann C, Knochel P. Z. Naturforsch., B 2013; 68: 411
1h Ellwart M, Knochel P. Angew. Chem. Int. Ed. 2015; 54: 10662

2a Lutter FH, Grassl S, Grokenberger L, Hofmayer MS, Chen YH, Knochel P. ChemCatChem 2019; 11: 5188
2b Wang ZX, Yang B. Org. Biomol. Chem. 2020; 18: 1057
2c Chen YH, Ellwart M, Malakhov V, Knochel P. Synthesis 2017; 49: 3215

3a Li J, Knochel P. Synthesis 2019; 51: 2100
3b Hammann JM, Hofmayer MS, Lutter FH, Thomas L, Knochel P. Synthesis 2017; 49: 3887
3c Kuzmina OM, Steib AK, Moyeux A, Cahiez G, Knochel P. Synthesis 2015; 47: 1696

4a Li GC, Szostak M. Chem. Eur. J. 2020; 26: 611
4b Colas K, dos Santos AC. V. D, Mendoza A. Org. Lett. 2019; 21: 7908
4c Kienle M, Dunst C, Knochel P. Org. Lett. 2009; 11: 5158

5a Haas D, Hammann JM, Greiner R, Knochel P. ACS Catal. 2016; 6: 1540
5b Dilman AD, Levin VV. Tetrahedron Lett. 2016; 57: 3986
5c Knochel P, Diene C. C. R. Chim. 2011; 14: 842
5d Knochel P, Blumke T, Groll K, Chen YH. Top. Organomet. Chem. 2013; 4: 173
5e Piontek A, Bisz E, Szostak M. Angew. Chem. Int. Ed. 2018; 57: 11116

6 Qian X, Yu ZL, Auffrant A, Gosmini C. Chem. Eur. J. 2013; 19: 6225
7 Benischke AD, Knoll I, Rerat A, Gosmini C, Knochel P. Chem. Commun. 2016; 52: 3171
8 Ziegler DS, Greiner R, Lumpe H, Kqiku L, Karaghiosoff K, Knochel P. Org. Lett. 2017; 19: 5760
9 Hofmayer MS, Hammann JM, Lutter FH, Knochel P. Synthesis 2017; 49: 3925
10 Greiner R, Ziegler DS, Cibu D, Jakowetz AC, Auras F, Bein T, Knochel P. Org. Lett. 2017; 19: 6384
11 Dong ZB, Balkenhohl M, Tan E, Knochel P. Org. Lett. 2018; 20: 7581
12 Li J, Konchel P. Angew. Chem. Int. Ed. 2018; 57: 11436
13 Liu XG, Zhou CJ, Lin E, Han XL, Zhang SS, Li QJ, Wang HG. Angew. Chem. Int. Ed. 2018; 57: 13096
14 Liu FP, Zhong JC, Zhou Y, Gao ZD, Walsh PJ, Wang XY, Ma SJ, Hou SC, Liu SZ, Wang MN, Wang M, Bian QH. Chem. Eur. J. 2018; 24: 2059
15 Lutter FH, Grokenberger L, Spiess P, Hammann JM, Karaghiosoff K, Knochel P. Angew. Chem. Int. Ed. 2020; 59: 5546
16 Grassl S, Chen YH, Hamze C, Tullmann CP, Knochel P. Org. Lett. 2019; 21: 494
17 Hofmayer MS, Sunagatullina A, Brosamlen D, Mauker P, Knochel P. Org. Lett. 2020; 22: 1286
18 Liu N, Wang L, Wang ZX. Chem. Commun. 2011; 47: 1598
19 Pekel OO, Erdik E. Tetrahedron Lett. 2011; 52: 7087
20 Zhang ZT, Qiao JF, Wang D, Han L, Ding R. Mol. Diversity 2014; 18: 245
21 Shi SC, Szostak M. Chem. Eur. J. 2016; 22: 10420
22 Hofmayer MS, Lutter FH, Grokenberger L, Hammann JM, Knochel P. Org. Lett. 2019; 21: 36
23 Melzig L, Metzger A, Knochel P. J. Org. Chem. 2010; 75: 2131
24 Huo HH, Gorsline BJ, Fu GC. Science 2020; 367: 559
25 An L, Tong FF, Zhang S, Zhang XG. J. Am. Chem. Soc. 2020; 142: 11884
26 Shi SC, Szostak M. Org. Lett. 2016; 18: 5872
27 Jung HS, Kim SH. Bull. Korean Chem. Soc. 2014; 35: 280
28 Barl NM, Malakhov V, Mathes C, Lustenberger P, Knochel P. Synthesis 2015; 47: 692
29 Zhou JR, Fu GC. J. Am. Chem. Soc. 2013; 125: 12527
30 Ikegami R, Koresawa A, Shibata T, Takagi K. J. Org. Chem. 2003; 68: 2195
31 Kabir MS, Monte A, Cook JM. Tetrahedron Lett. 2007; 48: 7269
32 Liu J, Deng Y, Wang HB, Zhang H, Yu GX, Wu BB, Zhang H, Li Q, Marder TB, Yang Z, Lei AW. Org. Lett. 2008; 10: 2661
33 Nitta J, Motohashi H, Aikawa K, Mikamia K. Asian J. Org. Chem. 2019; 8: 698
34 Benischke AD, Leroux M, Knoll I, Knochel P. Org. Lett. 2016; 18: 3626
35 Miao WJ, Zhao YC, Ni CF, Gao B, Zhang W, Hu JB. J. Am. Chem. Soc. 2018; 140: 880
36 Grassl S, Singer J, Knochel P. Angew. Chem. Int. Ed. 2019; 59: 335
37 Fu Y, Gou BL, Shi CZ, Du ZY, Shen T. ChemCatChem 2018; 10: 4253
38 Stathakis CI, Manolikakes SM, Knochel P. Org. Lett. 2013; 15: 1302
39 Erdik E, Pekel OO, Kalkan M. Appl. Organomet. Chem. 2009; 23: 245
40 Steib AK, Kuzmina OM, Fernandez S, Flubacher D, Knochel P. J. Am. Chem. Soc. 2013; 135: 15346
41 Steib AK, Fernandez S, Kuzmina OM, Corpet M, Gosmini C, Knochel P. Synlett 2015; 26: 1049
42 Bellan AB, Kuzmina OM, Vetsova VA, Knochel P. Synthesis 2017; 49: 188
43 Rong Z, Luo MM, Zeng XM. Org. Lett. 2019; 21: 6869
44 Wu WQ, Duong HA. Synlett 2018; 29: 1199
45 Kuzmina OM, Steib AK, Markiewicz JT, Flubacher D, Knochel P. Angew. Chem. Int. Ed. 2013; 52: 4945
46 Kuzmina OM, Steib AK, Fernandez S, Boudot W, Markiewicz JT, Knochel P. Chem. Eur. J. 2015; 21: 8242
47 Kuzmina OM, Steib AK, Flubacher D, Knochel P. Org. Lett. 2012; 14: 4818
48 An L, Xiao YL, Zhang S, Zhang XG. Angew. Chem. Int. Ed. 2018; 57: 6921
49 Bisz E, Szostak M. ChemSusChem 2018; 11: 1290
50 Bisz E, Szostak M. Green Chem. 2017; 19: 5361
51 Klatt T, Werner V, Maximova MG, Didier D, Apeloig Y, Knochel P. Chem. Eur. J. 2015; 21: 7830
52 Zhang MM, Gong J, Song RJ, Li JH. Eur. J. Org. Chem. 2014; 6769
53 Vulovic B, Cinderella AP, Watson DA. ACS Catal. 2017; 7: 8113
54 Dai QP, Zhao BG, Yang YH, Shi Y. Org. Lett. 2019; 21: 5157
55 Lesieur M, Slawin AM. Z, Cazin CS. J. Org. Biomol. Chem. 2014; 12: 5586
56 Dai WP, Xiao J, Jin GY, Wu JJ, Cao S. J. Org. Chem. 2014; 79: 10537
57 Iwasaki T, Fukuoka A, Min X, Yokoyama W, Kuniyasu H, Kambe N. Org. Lett. 2016; 18: 4868
58 Motohashi H, Mikami K. Org. Lett. 2018; 20: 5340
59 Baralle A, Otsuka S, Guerin V, Murakami K, Yorimitsu H, Osuka A. Synlett 2015; 26: 327
60 Kurata Y, Otsuka S, Fukui N, Nogi K, Yorimitsu H, Osuka A. Org. Lett. 2017; 19: 1274
61 Wang S, Xi CJ. Org. Lett. 2018; 20: 4131
62 Ghaleshahi HG, Antonacci G, Madsen R. Eur. J. Org. Chem. 2017; 1331
63 Antonacci G, Ahlburg A, Fristrup P, Norrby PO, Madsen R. Eur. J. Org. Chem. 2017; 4758
64 Erdik E, Pekel OO. Tetrahedron Lett. 2009; 50, 1501
65 Quinio P, Roman DS, Leon T, William S, Karaghiosoff K, Knochel P. Org. Lett. 2015; 17: 4396
66 Leibeling M, Shurrush KA, Werner V, Perrin L, Marek I. Angew. Chem. Int. Ed. 2016; 55: 6057
67 Leermann T, Leroux FR, Colobert F. Org. Lett. 2011; 13: 4479
68 Li GC, Szostak M. Org. Biomol. Chem. 2020; 18: 3827
69 Klatt T, Roman DS, Leon T, Knochel P. Org. Lett. 2014; 16: 1232
70 Castello-Mico A, Nafe J, Higashida K, Karaghiosoff K, Gingras M, Knochel P. Org. Lett. 2017; 19: 360
71 Balkenhohl M, Francois C, Roman DS, Quinio P, Knochel P. Org. Lett. 2017; 19: 536
72 Ellwart M, Hofner G, Gerwien A, Wanner KT, Knochel P. Synthesis 2017; 49: 5159
73 Balkenhohl M, Salgues B, Hirai T, Karaghiosoff K, Knochel P. Org. Lett. 2018; 20: 3114
74 Balkenhohl M, Valsamidou V, Knochel P. Eur. J. Org. Chem. 2019; 5165
75 Balkenhohl M, Heinz B, Abegg T, Knochel P. Org. Lett. 2018; 20: 8057
76 Heinz B, Balkenhohl M, Knochel P. Synthesis 2019; 51: 4452
77 Liu CW, Achtenhagen M, Szostak M. Org. Lett. 2016; 18: 2375
78 Dhayalan V, Samann C, Knochel P. Chem. Commun. 2015; 51: 3239
79 DeBerardinis AM, Turlington M, Pu L. Org. Lett. 2008; 10: 2709
80 Hatano M, Ito O, Suzuki S, Ishihara K. J. Org. Chem. 2010; 75: 5008
81 Nishimura RH. V, Murie VE, Soldi RA, Clososki GC. Synthesis 2015; 47: 1455
82 Quinio P, Kohout L, Roman DS, Gaar J, Karaghiosoff K, Knochel P. Synlett 2016; 27: 1715
83 Fu Y, Ma XZ, Shi CZ, Shen T, Du ZY. Appl. Organomet. Chem. 2018; 32: e4462
84 Juhasz K, Hell Z. Tetrahedron Lett. 2018; 59: 3136
85 Quinio P, Benischke AD, Moyeux A, Cahiez G, Knochel P. Synlett 2015; 26: 514
86 Benischke AD, Breuillac AJ. A, Moyeux A, Cahiez G, Knochel P. Synlett 2016; 27: 471
87 Hofmayer MS, Hammann JM, Haas D, Knochel P. Org. Lett. 2016; 18: 6456
88 Benischke AD, Desaintjean A, Juli T, Cahiez G, Knochel P. Synthesis 2017; 49: 5396
89 Desaintjean A, Belrhomari S, Rousseau L, Lefevre G, Knochel P. Org. Lett. 2019; 21: 8684
90 Rousseau L, Desaintjean A, Knochel P, Lefevre G. Molecules 2020; 25: 723
91 Groll K, Blumke TD, Unsinn A, Haas D, Knochel P. Angew. Chem. Int. Ed. 2012; 51: 11157
92 Shen ZL, Peng ZH, Yang CM, Helberg J, Mayer P, Marek I, Knochel P. Org. Lett. 2014; 16: 956
93 Minami H, Saito T, Wang C, Uchiyama M. Angew. Chem. Int. Ed. 2015; 54: 4665
94 Benischke AD, Anthore-Dalion L, Berionni G, Knochel P. Angew. Chem. Int. Ed. 2017; 56: 16390
95 Benischke AD, Anthore-Dalion L, Kohl F, Knochel P. Chem. Eur. J. 2018; 24: 11103
96 Wei BS, Zhang DC, Chen YH, Lei AW, Knochel P. Angew. Chem. Int. Ed. 2019; 58: 15631
97 Bellan AB, Knochel P. Synthesis 2019; 51: 3536
98 Anthore-Dalion L, Benischke AD, Wei BS, Berionni G, Knochel P. Angew. Chem. Int. Ed. 2019; 58: 4046
99 Shen ZL, Knochel P. Chem. Eur. J. 2015; 21: 7061