Progress on Iridium-Catalyzed Hydrosilylation of Alkenes and Alkynes

Weiwei Gao; Shengtao Ding

doi:10.1055/s-0040-1707239

Synthesis, Table of Contents

Synthesis 2020; 52(23): 3549-3563
DOI: 10.1055/s-0040-1707239

short review

Progress on Iridium-Catalyzed Hydrosilylation of Alkenes and Alkynes

Weiwei Gao

^aState Key Laboratory of Organic-Inorganic Composites, College of Chemical Engineering, Beijing University of Chemical Technology, Beijing, 100029, P. R. of China Email: stding@mail.buct.edu.cn

,

Shengtao Ding ∗

^aState Key Laboratory of Organic-Inorganic Composites, College of Chemical Engineering, Beijing University of Chemical Technology, Beijing, 100029, P. R. of China Email: stding@mail.buct.edu.cn

^bState Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing, 100191, P. R. of China

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Abstract

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Abstract

Hydrosilylation of multiple carbon–carbon bonds is a well-known process for the construction of organosilicon compounds. Nowadays, precious metal catalysts, especially platinum complexes, still occupy dominant positions in such processes. However, one important member of the precious metal family, iridium, is less used in this field. As early research mainly focused on developing stable and effective iridium catalysts, recent advances have disclosed the specific efficiency of simple iridium catalytic systems in the synthesis of functional organosilicon compounds. This short review summarizes the utilization of iridium complexes for the hydrosilylation of alkenes and alkynes, with an emphasis on the recent advances published in the last decade.

1 Introduction

2 Iridium-Catalyzed Hydrosilylation of Alkenes

3 Iridium-Catalyzed Hydrosilylation of Alkynes

4 Conclusions and Perspectives

Key words

iridium

catalysis

hydrosilylation

alkenes

alkynes

Full Text

References

References

For recent books, see:

1a Lee VY. Organosilicon Compounds: From Theory to Synthesis to Applications. Elsevier; Amsterdam: 2017
1b Hiyama T, Oestreich M. Organosilicon Chemistry: Novel Approaches and Reactions. Wiley-VCH; Weinheim: 2019

For selected books and reviews, see:

2a Marciniec B. Hydrosilylation: A Comprehensive Review on Recent Advances. Springer; Dordrecht: 2009
2b Troegel D, Stohrer J. Coord. Chem. Rev. 2011; 255: 1440
2c Greenhalgh MD, Jones AS, Thomas SP. ChemCatChem 2015; 7: 190
2d Nakajima Y, Shimada S. RSC Adv. 2015; 5: 20603
2e Sun J, Deng L. ACS Cat. 2016; 6: 290
2f Du X, Huang Z. ACS Cat. 2017; 7: 1227
2g Chen J, Guo J, Lu Z. Chin. J. Chem. 2018; 36: 1075
2h Obligacion JV, Chirik PJ. Nat. Rev. Chem. 2018; 2: 15

3 Chalk AJ, Harrod JF. J. Am. Chem. Soc. 1965; 87: 16
4 Marciniec B, Kownacki I. In Iridium Complexes in Organic Synthesis . Oro LA, Claver C. Wiley-VCH; Weinheim: 2009. Chap. 14, 345

5a Bauer A, Schäfer O, Kriegbaum M, Brader L, Pachaly B, Frey V. US6388119, 2002
5b Tonomura Y, Kubota T, Endo M. US6359161, 2002
5c Baumann F, Hoffmann M. EP1805190A1, 2007
5d Tonomura Y, Kubota T, Endo M. EP1156052B1, 2006
5e Baumann F. DE102005030581A1, 2007
5f Kornek T, Bauer A, Senden D. US7208618, 2007
5g Ramdani K, Vogin B, Guennount N. EP1515977B1, 2007
5h Ramdani K, Guennouni N, Vogin B. EP1637534B1, 2009
5i Ramdani K, Vogin B, Guennouni N. US7655813, 2010
5j Ramdani K, Vogin B, Guennount N. US7659418, 2010
5k Guennouni N, Galland J.-C. US7884225, 2011

6a Chalk AJ. Chem. Commun. 1969; 1207
6b Harrod JF, Gilson DF. R, Charles R. Can. J. Chem. 1969; 47: 2205
6c Harrod JF, Smith CA. J. Am. Chem. Soc. 1970; 92: 2699
6d Harrod JF, Smith CA. Can. J. Chem. 1970; 48: 870

7 Haszeldine RN, Parish RV, Parry DJ. J. Chem. Soc. A 1969; 683
8 Fernandez M.-J, Maitlis PM. Organometallics 1983; 2: 164
9 Harrod JF, Chalk AJ. J. Am. Chem. Soc. 1964; 86: 1776
10 Apple DC, Brady KA, Chance JM, Heard NE, Nile TA. J. Mol. Catal. 1985; 29: 55
11 Onderdelinden AL, van der Ent A. Inorg. Chim. Acta 1972; 6: 420
12 Oro LA, Fernández MJ, Esteruelas MA, Jiménez MS. J. Mol. Catal. 1986; 37: 151

13a Fernández MJ, Esteruelas MA, Jiménez MS, Oro LA. Organometallics 1986; 5: 1519
13b Fernández MJ, Esteruelas MA, Oro LA. Organometallics 1987; 6: 1751

14 Hostetler MJ, Bergman RG. J. Am. Chem. Soc. 1990; 112: 8621
15 Hostetler MJ, Butts MD, Bergman RG. Organometallics 1993; 12: 65
16 Tanke RS, Crabtree RH. Organometallics 1991; 10: 415
17 Tanke RS, Crabtree RH. J. Chem. Soc., Chem. Commun. 1990; 1056
18 Tanke RS, Crabtree RH. J. Am. Chem. Soc. 1990; 112: 7984
19 Szajek LP, Shapley JR. Organometallics 1994; 13: 1395

20a Kownacki I, Kubicki M, Marciniec B. Inorg. Chim. Acta 2002; 334: 301
20b Marciniec B, Kownacki I, Kubicki M. Organometallics 2002; 21: 3263

21 Pawluc P, Marciniec B, Kownacki I, Maciejewski H. Appl. Organomet. Chem. 2005; 19: 49
22 Kownacki I, Marciniec B, Macina A, Rubinsztajn S, Lamb D. Appl. Catal. A: Gen. 2007; 317: 53
23 Cipot J, Ferguson MJ, Stradiotto M. Inorg. Chim. Acta 2006; 359: 2780
24 Cipot J, McDonald R, Ferguson MJ, Schatte G, Stradiotto M. Organometallics 2007; 26: 594
25 Igarashi M, Matsumoto T, Kobayashi T, Sato K, Ando W, Shimada S, Hara M, Uchida H. J. Organomet. Chem. 2014; 752: 141
26 Riener K, Meister TK, Gigler P, Herrmann WA, Kühn FE. J. Catal. 2015; 331: 203
27 Muchnij JA, Kwaramba FB, Rahaim RJ. Org. Lett. 2014; 16: 1330
28 Xie X, Zhang X, Yang H, Ji X, Li J, Ding S. J. Org. Chem. 2019; 84: 1085
29 Perales JB, Van Vraken DL. J. Org. Chem. 2001; 66: 7270
30 Srinivas V, Nakajima Y, Sato K, Shimada S. Org. Lett. 2018; 20: 12
31 Song L.-J, Ding S, Wang Y, Zhang X, Wu Y.-D, Sun J. J. Org. Chem. 2016; 81: 6157
32 Zhang X, Gao C, Xie X, Liu Y, Ding S. Eur. J. Org. Chem. 2020; 556
33 Gao W, Zhang X, Xie X, Ding S. Chem. Commun. 2020; 56: 2012
34 Brady KA, Nile TA. J. Organomet. Chem. 1981; 206: 299
35 Fernández MJ, Oro LA. J. Mol. Catal. 1988; 45: 7
36 Jun C.-H, Crabtree RH. J. Organomet. Chem. 1993; 447: 177
37 Crabtree RH. New J. Chem. 2003; 27: 771

38a Ojima I, Clos N, Donovan RJ, Ingallina P. Organometallics 1990; 9: 3127
38b Hill JE, Nile TA. J. Organomet. Chem. 1977; 137: 293

39 Usón R, Oro LA, Carmona D, Esteruelas MA, Foces-Foces C, Cano FH, García-Blanco S. J. Organomet. Chem. 1983; 254: 249
40 Esteruelas MA, Nürnberg O, Oliván M, Oro LA, Werner H. Organometallics 1993; 12: 3264
41 Esteruelas MA, Oliván M, Oro LA, Tolosa JI. J. Organomet. Chem. 1995; 487: 143
42 Esteruelas MA, Lahoz FJ, Oñate E, Oro LA, Rodríguez L. Organometallics 1996; 15: 823
43 Esteruelas MA, Oliván M, Oro LA. Organometallics 1996; 15: 814
44 Martín M, Sola E, Torres O, Plou P, Oro LA. Organometallics 2003; 22: 5406
45 Martínez AP, Fabra MJ, García MP, Lahoz FJ, Oro LA, Teat SJ. Inorg. Chim. Acta 2005; 358: 1635
46 Field LD, Ward AJ. J. Organomet. Chem. 2003; 681: 91
47 Mas-Marzá E, Poyatos M, Sanaú M, Peris E. Inorg. Chem. 2004; 43: 2213
48 Mas-Marzá E, Sanaú M, Peris E. Inorg. Chem. 2005; 44: 9961
49 Viciano M, Mas-Marzá E, Sanaú M, Peris E. Organometallics 2006; 25: 3063
50 Zanardi A, Peris E, Mata JA. New J. Chem. 2008; 32: 120
51 Iglesias M, Pérez-Nicolás M, Miguel PJ. S, Polo V, Fernández-Alvarez FJ, Pérez-Torrente JJ, Oro LA. Chem. Commun. 2012; 48: 9480
52 Iglesias M, Miguel PJ. S, Polo V, Fernández-Alvarez FJ, Pérez-Torrente JJ, Oro LA. Chem. Eur. J. 2013; 19: 17559
53 Nguyen DH, Pérez-Torrente JJ, Jiménez MV, Modrego FJ, Gómez-Bautista D, Lahoz FJ, Oro LA. Organometallics 2013; 32: 6918
54 Pérez-Torrente JJ, Nguyen DH, Jiménez MV, Modrego FJ, Puerta-Oteo R, Gómez-Bautista D, Iglesias M, Oro LA. Organometallics 2016; 35: 2410
55 Sridevi VS, Fan WY, Leong WK. Organometallics 2007; 26: 1157
56 Scheeren C, Maasarani F, Hijazi A, Djukic J.-P, Pfeffer M. Organometallics 2007; 26: 3336
57 Corre Y, Werlé C, Brelot-Karmazin L, Djukic J.-P, Agbossou-Niedercorn F, Michon C. J. Mol. Catal. A: Chem. 2016; 423: 256
58 Miyake Y, Isomura E, Iyoda M. Chem. Lett. 2006; 35: 836
59 Xie X, Zhang X, Gao W, Meng C, Wang X, Ding S. Commun. Chem. 2019; 2: 101