Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2016; 48(04): 493-503
DOI: 10.1055/s-0035-1560556
DOI: 10.1055/s-0035-1560556
short review
Recent Progress in Palladium-Catalyzed Asymmetric Hydrophosphination
Further Information
Publication History
Received: 28 October 2015
Accepted after revision: 24 November 2015
Publication Date:
29 December 2015 (online)
Abstract
Asymmetric construction of P–C bonds is considered to be one of the most powerful methods for the preparation of chiral organophosphorus compounds. This review highlights recent progress in palladium-catalyzed asymmetric hydrophosphination reactions involving activated C=C bonds and diarylphosphines. The main catalytic systems employed for this protocol together with current substrate scope and mechanistic insights are described.
1 Introduction
2 Five-Membered CN/CP Palladacycle Catalyzed Protocols
3 PCP Pincer-Type Catalyst Based Protocols
4 NCN and PCN Pincers as Catalysts
5 Conclusion and Outlook
-
References
- 1a Lühr S, Holz J, Börner A. ChemCatChem 2011; 3: 1708
- 1b Rauchfuss T. Functionalized Tertiary Phosphines and Related Ligands in Organometallic Coordination Chemistry and Catalysis. In Homogeneous Catalysis with Metal Phosphine Complexes. Pignolet L. Springer; New York: 1983: 239-256
- 1c Kamer PC. J, van Leeuwen PW. N. M. Phosphorus(III) Ligands in Homogeneous Catalysis: Design and Synthesis. Wiley; Chichester: 2012
- 1d Imamoto T. J. Synth. Org. Chem., Jpn. 2007; 65: 1060
- 1e Hayashi T. Acc. Chem. Res. 2000; 33: 354
- 2a Glueck D. Synlett 2007; 2627
- 2b Koshti V, Gaikwad S, Chikkali SH. Coord. Chem. Rev. 2014; 265: 52
- 2c Rosenberg L. ACS Catal. 2013; 3: 2845
- 2d Glueck DS. Chem. Eur. J. 2008; 14: 7108
- 3 Kovacik I, Wicht DK, Grewal NS, Glueck DS, Incarvito CD, Guzei IA, Rheingold AL. Organometallics 2000; 19: 950
- 4 Scriban C, Kovacik I, Glueck DS. Organometallics 2005; 24: 4871
- 5a Sadow AD, Haller I, Fadini L, Togni A. J. Am. Chem. Soc. 2004; 126: 14704
- 5b Sadow AD, Togni A. J. Am. Chem. Soc. 2005; 127: 17012
- 6a Bartoli G, Bosco M, Carlone A, Locatelli M, Mazzanti A, Sambri L, Melchiorre P. Chem. Commun. 2007; 722
- 6b Carlone A, Bartoli G, Bosco M, Sambri L, Melchiorre P. Angew. Chem. Int. Ed. 2007; 46: 4504
- 6c Ibrahem I, Rios R, Vesely J, Hammar P, Eriksson L, Himo F, Cordova A. Angew. Chem. Int. Ed. 2007; 46: 4507
- 6d Ibrahem I, Hammar P, Vesely J, Rios R, Eriksson L, Cordova A. Adv. Synth. Catal. 2008; 350: 1875
- 7 Enders D, Saint-Dizier A, Lannou M.-I, Lenzen A. Eur. J. Org. Chem. 2006; 29
- 8a Leung P.-H. Acc. Chem. Res. 2004; 37: 169
- 8b Ma M, Pullarkat SA, Li Y, Leung P.-H. Inorg. Chem. 2007; 46: 9488
- 8c Ma M, Pullarkat SA, Yuan M, Zhang N, Li Y, Leung P.-H. Organometallics 2009; 28: 4886
- 8d Ma M, Pullarkat SA, Li Y, Leung P.-H. Eur. J. Inorg. Chem. 2010; 1865
- 8e Ma M, Zhang N, Li Y, Pullarkat SA, Leung P.-H. Organometallics 2015; 34: 5081
- 9 Pullarkat S, Leung P.-H. Top. Organomet. Chem. 2013; 43: 145
- 10 Huang Y, Pullarkat SA, Li Y, Leung P.-H. Chem. Commun. 2010; 46: 6950
- 11 Huang Y, Pullarkat SA, Li Y, Leung P.-H. Inorg. Chem. 2012; 51: 2533
- 12 Jia Y.-X, Li B.-B, Li Y, Pullarkat SA, Xu K, Hirao H, Leung P.-H. Organometallics 2014; 33: 6053
- 13 Sabater S, Mata JA, Peris E. Organometallics 2013; 32: 1112
- 14 Huang Y, Pullarkat SA, Teong S, Chew RJ, Li Y, Leung P.-H. Organometallics 2012; 31: 4871
- 15 Huang Y, Chew RJ, Li Y, Pullarkat SA, Leung P.-H. Org. Lett. 2011; 13: 5862
- 16 Yang X.-Y, Tay WS, Li Y, Pullarkat SA, Leung P.-H. Organometallics 2015; 34: 1582
- 17 Chew RJ, Teo KY, Huang Y, Li B.-B, Li Y, Pullarkat SA, Leung P.-H. Chem. Commun. 2014; 50: 8768
- 18 Chew RJ, Lu Y, Jia Y.-X, Li B.-B, Wong EH. Y, Goh R, Li Y, Huang Y, Pullarkat SA, Leung P.-H. Chem. Eur. J. 2014; 20: 14514
- 19 Gan K, Sadeer A, Xu C, Li Y, Pullarkat SA. Organometallics 2014; 33: 5074
- 20 Chew RJ, Li X.-R, Li Y, Pullarkat SA, Leung P.-H. Chem. Eur. J. 2015; 21: 4800
- 21a Arseniyadis S, Valleix A, Wagner A, Mioskowski C. Angew. Chem. Int. Ed. 2004; 43: 3314
- 21b Trost BM, Toste FD. J. Am. Chem. Soc. 1999; 121: 4545
- 22 Swain CG, Swain MS, Powell AL, Alunni S. J. Am. Chem. Soc. 1983; 105: 502
- 23 Bürgi HB, Dunitz JD, Lehn JM, Wipff G. Tetrahedron 1974; 30: 1563
- 24 Chew RJ, Sepp K, Li B.-B, Li Y, Zhu P.-C, Tan NS, Leung P.-H. Adv. Synth. Catal. 2015; 357: 3297
- 25 Xu C, Jun Hao Kennard G, Hennersdorf F, Li Y, Pullarkat SA, Leung P.-H. Organometallics 2012; 31: 3022
- 26 Huang Y, Chew RJ, Pullarkat SA, Li Y, Leung P.-H. J. Org. Chem. 2012; 77: 6849
- 27 Chew RJ, Huang Y, Li Y, Pullarkat SA, Leung P.-H. Adv. Synth. Catal. 2013; 355: 1403
- 28 Chooi SY. M, Siah SY, Leung PH, Mok KF. Inorg. Chem. 1993; 32: 4812
- 29 Feng J.-J, Chen X.-F, Shi M, Duan W.-L. J. Am. Chem. Soc. 2010; 132: 5562
- 30 Du D, Duan W.-L. Chem. Commun. 2011; 47: 11101
- 31 Huang M, Li C, Huang J, Duan W.-L, Xu S. Chem. Commun. 2012; 48: 11148
- 32 Cho B, Tan C.-H, Wong MW. Org. Biomol. Chem. 2011; 9: 4550
- 33 Feng J.-J, Huang M, Lin Z.-Q, Duan W.-L. Adv. Synth. Catal. 2012; 354: 3122
- 34 Ding B, Zhang Z, Xu Y, Liu Y, Sugiya M, Imamoto T, Zhang W. Org. Lett. 2013; 15: 5476
- 35 Xu Y, Yang Z, Ding B, Liu D, Liu Y, Sugiya M, Imamoto T, Zhang W. Tetrahedron 2015; 71: 6832
- 36 Du D, Lin Z.-Q, Lu J.-Z, Li C, Duan W.-L. Asian J. Org. Chem. 2013; 2: 392
- 37 Lu J, Ye J, Duan W.-L. Org. Lett. 2013; 15: 5016
- 38 Lu J, Ye J, Duan W.-L. Chem. Commun. 2014; 50: 698
- 39 Yang X.-Y, Gan JH, Li Y, Pullarkat SA, Leung P.-H. Dalton Trans. 2015; 44: 1258
- 40 Yang X.-Y, Tay WS, Li Y, Pullarkat SA, Leung P.-H. Organometallics 2015; 34: 5196
- 41 Jia Y.-X, Yang X.-Y, Tay WS, Li Y, Pullarkat SA, Xu K, Hirao H, Leung P.-H. Dalton Trans. 2016; 45 DOI: 10.1039/C5DT02049B
- 42 Li C, Bian Q.-L, Xu S, Duan W.-L. Org. Chem. Front. 2014; 1: 541
- 43 Hao X.-Q, Zhao Y.-W, Yang J.-J, Niu J.-L, Gong J.-F, Song M.-P. Organometallics 2014; 33: 1801
- 44 Hao XQ, Huang JJ, Wang T, Lv J, Gong JF, Song MP. J. Org. Chem. 2014; 79: 9512
For selected examples, see: