Transition-Metal-Catalyzed Stereo- and Regioselective Hydrosilylation of Unsymmetrical Alkynes

Peng He; Meng-Yang Hu; Xin-Yu Zhang; Shou-Fei Zhu

doi:10.1055/a-1605-9572

Synthesis, Table of Contents

Synthesis 2022; 54(01): 49-66
DOI: 10.1055/a-1605-9572

short review

Transition-Metal-Catalyzed Stereo- and Regioselective Hydrosilylation of Unsymmetrical Alkynes

Peng He

,

Meng-Yang Hu

,

Xin-Yu Zhang

,

Shou-Fei Zhu ∗

Abstract

All articles of this category

Dedicated to the 100^th Anniversary of Chemistry at Nankai University.

Abstract

Alkyne hydrosilylation is one of the most efficient methods for the synthesis of alkenyl silicon derivatives and has been a hot topic of research for decades. This short review summarizes the progress in transition-metal-catalyzed stereo- and regioselective hydrosilylation of unsymmetrical alkynes. Topics are discussed based on different types of alkynes and the selectivities.

1 Introduction

2 Terminal Alkyne Hydrosilylation

2.1 β-E Selectivity

2.2 β-Z Selectivity

2.3 α-selectivity

3 Internal Alkyne Hydrosilylation

3.1 Aryl–Alkyl Acetylenes

3.2 Alkyl–Alkyl Acetylenes

3.3 Internal Alkynes with Polarized Substituents

4 Summary and Outlook

Key words

hydrosilylation - transition-metal catalysts - alkynes - alkenyl silicons - selectivity

Full Text

References

References
1 Luh T.-Y, Liu S.-T. Synthetic Applications of Allylsilanes and Vinylsilanes. In The Chemistry of Organic Silicon Compounds, Vol. 1. Wiley; Weinheim: 1998: 1793
2 Langkopf E, Schinzer D. Chem. Rev. 1995; 95: 1375
3 Anderson E, Lim D. Synthesis 2012; 44: 983
4 Marciniec B. Hydrosilylation: A Comprehensive Review on Recent Advances. Springer; Dordrecht: 2009
5 de Almeida LD, Wang HL, Junge K, Cui XJ, Beller M. Angew. Chem. Int. Ed. 2021; 60: 550
6 Cui C, Li J, Chen W. Synlett 2021; 32: 962
7 Gao WW, Ding ST. Synthesis 2020; 52: 3549
8 Wen HA, Liu GX, Huang Z. Coord. Chem. Rev. 2019; 386: 138
9 Chen J, Guo J, Lu Z. Chin. J. Chem. 2018; 36: 1075
10 Sun J, Deng L. ACS Catal. 2016; 6: 290
11 Zaranek M, Marciniec B, Pawluć P. Org. Chem. Front. 2016; 3: 1337
12 Greenhalgh MD, Jones AS, Thomas SP. ChemCatChem 2015; 7: 190
13 Trost BM, Ball ZT. Synthesis 2005; 853
14 Rummelt SM, Radkowski K, Roşca D.-A, Fürstner A. J. Am. Chem. Soc. 2015; 137: 5506
15 Trost BM, Ball ZT, Joge T. Angew. Chem. Int. Ed. 2003; 42: 3415
16 Trost BM, Ball ZT. J. Am. Chem. Soc. 2003; 125: 30
17 Denmark SE, Pan W. Org. Lett. 2001; 3: 61
18 Na Y, Chang S. Org. Lett. 2000; 2: 1887
19 Marshall JA, Yanik MM. Org. Lett. 2000; 2: 2173
20 Tamao K, Maeda K, Tanaka T, Ito Y. Tetrahedron Lett. 1988; 29: 6955
21 Arii H, Nakabayashi K, Mochida K, Kawashima T. Molecules 2016; 21: 999
22 Trost BM, Ball ZT. J. Am. Chem. Soc. 2001; 123: 12726
23 Trost BM, Ball ZT, Joge T. J. Am. Chem. Soc. 2002; 124: 7922
24 Chung LW, Wu YD, Trost BM, Ball ZT. J. Am. Chem. Soc. 2003; 125: 11578
25 Trost BM, Ball ZT, Laemmerhold KM. J. Am. Chem. Soc. 2005; 127: 10028
26 Xie X, Zhang X, Gao W, Meng C, Wang X, Ding S. Commun. Chem. 2019; 2: 101
27 Chalk AJ, Harrod JF. J. Am. Chem. Soc. 1965; 87: 16
28 Benkeser RA, Burrous ML, Nelson LE, Swisher JV. J. Am. Chem. Soc. 1961; 83: 4385
29 Iovel IG, Goldberg YS, Shymanska MV, Lukevics E. Organometallics 1987; 6: 1410
30 Tojo S, Isobe M. Tetrahedron Lett. 2005; 46: 381
31 Green M, Spencer JL, Stone FG. A, Tsipis CA. J. Chem. Soc., Dalton Trans. 1977; 1525
32 Lewis LN, Sy KG, Bryant GL, Donahue PE. Organometallics 1991; 10: 3750
33 Itami K, Mitsudo K, Nishino A, Yoshida J. J. Org. Chem. 2002; 67: 2645
34 Dierick S, Vercruysse E, Berthon-Gelloz G, Markó IE. Chem. Eur. J. 2015; 21: 17073
35 De Bo G, Berthon-Gelloz G, Tinant B, Markó IE. Organometallics 2006; 25: 1881
36 Berthon-Gelloz G, Schumers JM, De Bo G, Markó IE. J. Org. Chem. 2008; 73: 4190
37 Munz D, Allolio C, Meyer D, Micksch M, Roessner L, Strassner T. J. Organomet. Chem. 2015; 794: 330
38 Zhang F, Bai Y, Yang X, Li J, Peng J. Phosphorus, Sulfur Silicon Relat. Elem. 2017; 192: 1271
39 Aneetha H, Wu W, Verkade JG. Organometallics 2005; 24: 2590
40 Hamze A, Provot O, Brion J.-D, Alami M. J. Organomet. Chem. 2008; 693: 2789
41 Blug M, Le Goff X.-F, Mézailles N, Le Floch P. Organometallics 2009; 28: 2360
42 Ortega-Moreno L, Peloso R, Maya C, Suárez A, Carmona E. Chem. Commun. 2015; 51: 17008
43 Watanabe H, Kitahara T, Motegi T, Nagai Y. J. Organomet. Chem. 1977; 139: 215
44 Chance JM, Nile TA. J. Mol. Catal. 1987; 42: 91
45 Takeuchi R, Tanouchi N. J. Chem. Soc., Perkin Trans. 1 1994; 2909
46 Mori A, Takahisa E, Yamamura Y, Kato T, Mudalige AP, Kajiro H, Hirabayashi K, Nishihara Y, Hiyama T. Organometallics 2004; 23: 1755
47 Mori A, Takahisa E, Kajiro H, Hirabayashi K, Nishihara Y, Hiyama T. Chem. Lett. 1998; 27: 443
48 Ojima I, Clos N, Donovan RJ, Ingallina P. Organometallics 1990; 9: 3127
49 Faller JW, D’Alliessi DG. Organometallics 2002; 21: 1743
50 Murai T, Nagaya E, Shibahara F, Maruyama T, Nakazawa H. J. Organomet. Chem. 2015; 794: 76
51 Morales-Cerón JP, Lara P, López-Serrano J, Santos LL, Salazar V, Álvarez E, Suárez A. Organometallics 2017; 36: 2460
52 Corre Y, Werlé C, Brelot-Karmazin L, Djukic J.-P, Agbossou-Niedercorn F, Michon C. J. Mol. Catal. A: Chem. 2016; 423: 256
53 Esteruelas MA, Oro LA, Valero C. Organometallics 1991; 10: 462
54 Katayama H, Taniguchi K, Kobayashi M, Sagawa T, Minami T, Ozawa F. J. Organomet. Chem. 2002; 645: 192
55 Gao R, Pahls DR, Cundari TR, Yi CS. Organometallics 2014; 33: 6937
56 Yamashita H, Uchimaru Y. Chem. Commun. 1999; 1763
57 Motoda D, Shinokubo H, Oshima K. Synlett 2002; 1529
58 Wu G, Chakraborty U, Jacobi von Wangelin A. Chem. Commun. 2018; 54: 12322
59 Wu C, Teo WJ, Ge S. ACS Catal. 2018; 8: 5896
60 Guo J, Wang H, Xing S, Hong X, Lu Z. Chem 2019; 5: 881
61 Li R.-H, An X.-M, Yang Y, Li D.-C, Hu Z.-L, Zhan Z.-P. Org. Lett. 2018; 20: 5023
62 Mo Z, Xiao J, Gao Y, Deng L. J. Am. Chem. Soc. 2014; 136: 17414
63 Docherty JH, Peng J, Dominey AP, Thomas SP. Nat. Chem. 2017; 9: 595
64 Bartik T, Nagy G, Kvintovics P, Happ B. J. Organomet. Chem. 1993; 453: 29
65 Chaulagain MR, Mahandru GM, Montgomery J. Tetrahedron 2006; 62: 7560
66 Wang H, Huang Y, Wang X, Cui X, Shi F. Org. Biomol. Chem. 2020; 18: 7554
67 Zhou Y.-B, Liu Z.-K, Fan X.-Y, Li R.-H, Zhang G.-L, Chen L, Pan Y.-M, Tang H.-T, Zeng J.-H, Zhan Z.-P. Org. Lett. 2018; 20: 7748
68 Hu M.-Y, He P, Qiao T.-Z, Sun W, Li W.-T, Lian J, Li J.-H, Zhu S.-F. J. Am. Chem. Soc. 2020; 142: 16894
69 Hu M.-Y, Lian J, Sun W, Qiao T.-Z, Zhu S.-F. J. Am. Chem. Soc. 2019; 141: 4579
70 Takahashi T, Bao F, Gao G, Ogasawara M. Org. Lett. 2003; 5: 3479
71 Wang Z.-L, Zhang F.-L, Xu J.-L, Shan C.-C, Zhao M, Xu Y.-H. Org. Lett. 2020; 22: 7735
72 Levine DS, Tilley TD, Andersen RA. Chem. Commun. 2017; 53: 11881
73 Hu M.-Y, He Q, Fan S.-J, Wang Z.-C, Liu L.-Y, Mu Y.-J, Peng Q, Zhu S.-F. Nat. Commun. 2018; 9: 221
74 Zou H.-N, Zhu S.-F. Prog. Chem. 2020; 32: 1766
75 Mas-Marzá E, Sanaú M, Peris E. Inorg. Chem. 2005; 44: 9961
76 McBee JL, Escalada J, Tilley TD. J. Am. Chem. Soc. 2009; 131: 12703
77 Bartlewicz O, Jankowska-Wajda M, Maciejewski H. Catalysts 2020; 10: 608
78 Puerta-Oteo R, Munarriz J, Polo V, Jiménez MV, Pérez-Torrente JJ. ACS Catal. 2020; 10: 7367
79 Sánchez-Page B, Munarriz J, Jiménez MV, Perez-Torrente JJ, Blasco J, Subias G, Passarelli V, Álvarez P. ACS Catal. 2020; 10: 13334
80 Apple DC, Brady KA, Chance JM, Heard NE, Nile TA. J. Mol. Catal. 1985; 29: 55
81 Tanke RS, Crabtree RH. J. Am. Chem. Soc. 1990; 112: 7984
82 Zanardi A, Peris E, Mata JA. New J. Chem. 2008; 32: 120
83 Navarro M, Smith CA, Albrecht M. Inorg. Chem. 2017; 56: 11688
84 Pérez-Torrente JJ, Nguyen DH, Jiménez MV, Modrego FJ, Puerta-Oteo R, Gómez-Bautista D, Iglesias M, Oro LA. Organometallics 2016; 35: 2410
85 Iglesias M, Sanz Miguel PJ, Polo V, Fernández-Alvarez FJ, Pérez-Torrente JJ, Oro LA. Chem. Eur. J. 2013; 19: 17559
86 Iglesias M, Pérez-Nicolás M, Miguel PJ. S, Polo V, Fernández-Alvarez FJ, Pérez-Torrente JJ, Oro LA. Chem. Commun. 2012; 48: 9480
87 Jun C.-H, Crabtree RH. J. Organomet. Chem. 1993; 447: 177
88 Esteruelas MA, López AM, Oro LA, Tolosa J. J. Mol. Catal. A: Chem. 1995; 96: 21
89 Maifeld SV, Tran MN, Lee D. Tetrahedron Lett. 2005; 46: 105
90 Aricó CS, Cox LR. Org. Biomol. Chem. 2004; 2: 2558
91 Mutoh Y, Mohara Y, Saito S. Org. Lett. 2017; 19: 5204
92 Yang YF, Chung LW, Zhang X, Houk KN, Wu YD. J. Org. Chem. 2014; 79: 8856
93 Challinor AJ, Calin M, Nichol GS, Carter NB, Thomas SP. Adv. Synth. Catal. 2016; 358: 2404
94 Greenhalgh MD, Frank DJ, Thomas SP. Adv. Synth. Catal. 2014; 356: 584
95 Teo WJ, Wang C, Tan YW, Ge S. Angew. Chem. Int. Ed. 2017; 56: 4328
96 Du X, Hou W, Zhang Y, Huang Z. Org. Chem. Front. 2017; 4: 1517
97 Yang X, Wang C. Angew. Chem. Int. Ed. 2018; 57: 923
98 Zhang XY, Ji X, Xie XZ, Ding ST. Chem. Commun. 2018; 54: 12958
99 Sore HF, Blackwell DT, Macdonald SJ, Spring DR. Org. Lett. 2010; 12: 2806
100 Trost BM, Ball ZT. J. Am. Chem. Soc. 2005; 127: 17644
101 Kawanami Y, Sonoda Y, Mori T, Yamamoto K. Org. Lett. 2002; 4: 2825
102 Menozzi C, Dalko PI, Cossy J. J. Org. Chem. 2005; 70: 10717
103 Wada F, Abe S, Yonemaru N, Kikukawa K, Matsuda T. Bull. Chem. Soc. Jpn. 1991; 64: 1701
104 Iglesias M, Aliaga-Lavrijsen M, Miguel PJ. S, Fernández-Alvarez FJ, Pérez-Torrente JJ, Oro LA. Adv. Synth. Catal. 2015; 357: 350
105 Rivera-Claudio M, Rozell J, Ramirez-Oliva E, Cervantes J, Pannell KH. J. Organomet. Chem. 1996; 521: 267
106 Rivero-Crespo MA, Leyva-Pérez A, Corma A. Chem. Eur. J. 2017; 23: 1702
107 Guo J, Shen X, Lu Z. Angew. Chem. Int. Ed. 2017; 56: 615
108 Guo J, Lu Z. Angew. Chem. Int. Ed. 2016; 55: 10835
109 Zuo Z, Yang J, Huang Z. Angew. Chem. Int. Ed. 2016; 55: 10839
110 Wen HA, Wan XL, Huang Z. Angew. Chem. Int. Ed. 2018; 57: 6319
111 Zhang S, Ibrahim JJ, Yang Y. Org. Lett. 2018; 20: 6265
112 Skrodzki M, Patroniak V, Pawluc P. Org. Lett. 2021; 23: 663
113 Zong Z, Yu Q, Sun N, Hu B, Shen Z, Hu X, Jin L. Org. Lett. 2019; 21: 5767
114 Wang D, Lai Y, Wang P, Leng X, Xiao J, Deng L. J. Am. Chem. Soc. 2021; 143: 12847
115 Berding J, van Paridon JA, van Rixel VH. S, Bouwman E. Eur. J. Inorg. Chem. 2011; 2450
116 Rivera-Hernández A, Fallon BJ, Ventre S, Simon C, Tremblay MH, Gontard G, Derat E, Amatore M, Aubert C, Petit M. Org. Lett. 2016; 18: 4242
117 Yong L, Kirleis K, Butenschön H. Adv. Synth. Catal. 2006; 348: 833
118 Molander GA, Retsch WH. Organometallics 1995; 14: 4570
119 Ding S, Song L.-J, Chung LW, Zhang X, Sun J, Wu Y.-D. J. Am. Chem. Soc. 2013; 135: 13835
120 Ding S, Song L.-J, Wang Y, Zhang X, Chung L.-W, Wu Y.-D, Sun J. Angew. Chem. Int. Ed. 2015; 54: 5632
121 Song L.-J, Ding S, Wang Y, Zhang X, Wu Y.-D, Sun J. J. Org. Chem. 2016; 81: 6157
122 Huang K.-H, Isobe M. Eur. J. Org. Chem. 2014; 4733
123 Hosokawa S, Isobe M. Tetrahedron Lett. 1998; 39: 2609
124 Konno T, Taku K.-i, Yamada S, Moriyasu K, Ishihara T. Org. Biomol. Chem. 2009; 7: 1167