Palladium-Catalyzed Asymmetric 1,4-Addition of Diarylphosphines to α,β-Unsaturated Sulfonyl Fluorides

Dedicated to Professor Guoqiang Lin on the occasion of his 80^th birthday

Abstract

A Pd-catalyzed asymmetric phosphination of α,β-unsaturated sulfonyl fluorides was developed, and a series of tertiary phosphorus compounds were obtained in excellent yields and enantioselectivities (up to 99% ee). The chiral adduct can be further converted into chiral phosphine sulfonic acid as the ligand for the arene Ru metal complex.

Key words

α,β-unsaturated sulfonyl fluoride - asymmetric 1,4-addition - palladium catalyst - chiral phosphine

• References

• 1a Phosphorus Ligands in Asymmetric Catalysis: Synthesis and Applications, Vol. 1–3. Börner A. Wiley-VCH; Weinheim: 2008
• 1b Phosphorus(III) Ligands in Homogeneous Catalysis . Kamer PC. J, van Leeuwen PW. N. M. Wiley; Chichester: 2012

For reviews on hybrid phosphine ligands, see:
• 2a Wassenaar J, Reek JN. H. Org. Biomol. Chem. 2011; 9: 1704
• 2b Dieguez M, Pamies O. Isr. J. Chem. 2012; 52: 572
• 3a Ma Y.-N, Li S.-X, Yang S.-D. Acc. Chem. Res. 2017; 50: 1480

For selected examples of transition-metal-catalyzed C–H activation of organophosphorus compounds, see:
• 3b Kuninobu Y, Yoshida T, Takai K. J. Org. Chem. 2011; 76: 7370
• 3c Baba K, Tobisu M, Chatani N. Angew. Chem. Int. Ed. 2013; 52: 11892
• 3d Feng C.-G, Ye M, Xiao K.-J, Li S, Yu J.-Q. J. Am. Chem. Soc. 2013; 135: 9322
• 3e Li C, Yano T, Ishida N, Murakami M. Angew. Chem. Int. Ed. 2013; 52: 9801
• 3f Gwon D, Lee D, Kim J, Park S, Chang S. Chem. Eur. J. 2014; 20: 12421
• 3g Qiu X, Wang M, Zhao Y, Shi Z. Angew. Chem. Int. Ed. 2017; 56: 7233
• 3h Wen J, Wang D, Qian J, Wang D, Zhu C, Zhao Y, Shi Z. Angew. Chem. Int. Ed. 2019; 58: 2078

For reviews on the use of phosphine sulfonate ligands in catalytic reactions, see:
• 4a Nakamura A, Anselment TM, Claverie J, Goodall B, Jordan RF, Mecking S, Rieger B, Sen A, van Leeuwen PW. N. M, Nozaki K. Acc. Chem. Res. 2013; 46: 1438
• 4b Nakamura A, Ito S, Nozaki K. Chem. Rev. 2009; 109: 5215
• 5 For an example of synthesis and application of chiral phosphine sulfonate ligand, see: Nakamura A, Kageyama T, Goto H, Carrow BP, Ito S, Nozaki K. J. Am. Chem. Soc. 2012; 134: 12366

For catalytic asymmetric 1,4-addition of substituted phosphines or phosphine oxides to electron-deficient alkenes, see:
• 6a Carlone A, Bartoli G, Bosco M, Sambri L, Melchiorre P. Angew. Chem. Int. Ed. 2007; 46: 4504
• 6b Ibrahem I, Rios R, Vesely J, Hammar P, Eriksson L, Himo F, Córdova A. Angew. Chem. Int. Ed. 2007; 46: 4507
• 6c Bartoli G, Bosco M, Carlone A, Locatelli M, Mazzanti A, Sambri L, Melchiorre P. Chem. Commun. 2007; 722
• 6d Fu X, Jiang Z, Tan C.-H. Chem. Commun. 2007; 5058
• 6e Ibrahem I, Hammar P, Vesely J, Rios R, Eriksso L, Córdova A. Adv. Synth. Catal. 2008; 350: 1875
• 6f Zhao D, Mao L, Yang D, Wang R. J. Org. Chem. 2010; 75: 6756
• 6g Wen S, Li L, Wu H, Yu F, Liang X, Ye J. Chem. Commun. 2010; 4806
• 6h Huang Y, Pullarkat SA, Li L, Leung P.-H. Chem. Commun. 2010; 6950
• 6i Russo A, Lattanzi A. Eur. J. Org. Chem. 2010; 6736
• 6j Luo X, Zhou Z, Li X, Liang X, Ye J. RSC Adv. 2011; 1: 698
• 6k Yang M.-J, Liu Y.-J, Gong J.-F, Song M.-P. Organometallics 2011; 30: 3793
• 6l Huang Y, Chew RJ, Li Y, Pullarkat SA, Leung P.-H. Org. Lett. 2011; 13: 5862
• 6m Huang Y, Pullarkat SA, Li Y, Leung P.-H. Inorg. Chem. 2012; 51: 2533
• 6n Zhao D, Wang L, Yang D, Zhang Y, Wang R. Chem. Asian. J. 2012; 7: 881
• 6o Huang Y, Pullarkat SA, Teong S, Chew RJ, Li Y, Leung P.-H. Organometallics 2012; 31: 4871
• 6p Huang Y, Pullarkat SA, Chew RJ, Li Y, Leung P.-H. J. Org. Chem. 2012; 77: 6894
• 6q Hatano M, Horibe T, Ishihara K. Angew. Chem. Int. Ed. 2013; 52: 4549
• 6r Chew RJ, Huang Y, Li Y, Pullarkat SA, Leung P.-H. Adv. Synth. Catal. 2013; 355: 1403
• 6s Ding B, Zhang Z, Xu Y, Liu Y, Sugiya M, Imamoto T, Zhang W. Org. Lett. 2013; 15: 5476
• 6t Chew RJ, Teo KY, Huang Y, Li B.-B, Li Y, Pullarkat SA, Leung P.-H. Chem. Commun. 2014; 50: 8768
• 6u 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
• 6v Hao X.-Q, Zhao Y.-W, Yang J.-J, Niu J.-L, Gong J.-F, Song M.-P. Organometallics 2014; 33: 1801
• 6w Hao X.-Q, Huang J.-J, Wang T, Lv J, Gong J.-F, Song M.-P. J. Org. Chem. 2014; 79: 9512
• 6x Xu Y, Yang Z, Ding B, Liu D, Liu Y, Sugiya M, Imamoto T, Zhang W. Tetrahedron 2015; 71: 6832
• 6y Yue W.-J, Xiao J.-Z, Zhang S, Yin L. Angew. Chem. Int. Ed. 2020; 58: 7057
• 6z Li Y.-B, Tian H, Yin L. J. Am. Chem. Soc. 2020; 142: 20098
• 7a Feng J.-J, Chen X.-F, Shi M, Duan W.-L. J. Am. Chem. Soc. 2010; 132: 5562
• 7b Du D, Duan W.-L. Chem. Commun. 2011; 47: 11101
• 7c Chen Y.-R, Duan W.-L. Org. Lett. 2011; 13: 5824
• 7d Feng J.-J, Huang M, Lin Z.-Q, Duan W.-L. Adv. Synth. Catal. 2012; 354: 3122
• 7e Huang M, Li C, Duan W.-L, Xu S. Chem. Commun. 2012; 48: 11148
• 7f Du D, Lin Z.-Q, Lu J.-Z, Li C, Duan W.-L. Asian J. Org. Chem. 2013; 2: 392
• 7g Lu J, Ye J, Duan W.-L. Chem. Commun. 2014; 50: 698
• 7h Li C, Li W.-X, Xu S, Duan W.-L. Org. Chem. Front. 2014; 1: 541
• 7i Chen Y.-R, Feng J.-J, Duan W.-L. Tetrahedron Lett. 2014; 55: 595
• 7j Song Y.-C, Dai G.-F, Xiao F, Duan W.-L. Tetrahedron Lett. 2016; 57: 2990
• 7k Wei X, Duan W.-L. Synthesis 2016; 48: 4155
• 7l Wang C, Huang K, Ye J, Duan W.-L. J. Am. Chem. Soc. 2021; 143: 5685
• 8a Lu J, Ye J, Duan W.-L. Org. Lett. 2013; 15: 5016
• 8b Dai G..-F, Xiao F, Duan W.-L. Synthesis 2018; 50: 3506
• 9 Dong J, Krasnova L, Finn MG, Sharpless KB. Angew. Chem. Int. Ed. 2014; 53: 9430
• 10 Li X.-R, Chen HJ, Wang W, Ma M, Chen Y, Li Y, Pullarkat SA, Leung P.-H. J. Organomet. Chem. 2019; 89: 120912

For the synthesis and application of the chiral PCP–PdCl complex, see:
• 11a Longmire JM, Zhang X. Tetrahedron Lett. 1997; 38: 1725
• 11b Longmire JM, Zhang X, Shang M. Organometallics 1998; 17: 4374