Synthesis of α,β-Unsaturated Phosphine Sulfides

Xian-Liang Wang; Jin-Xiang Chen; Xue-Shun Jia; Liang Yin

doi:10.1055/s-0039-1690685

Synthesis, Table of Contents

Synthesis 2020; 52(01): 141-149
DOI: 10.1055/s-0039-1690685

paper

Synthesis of α,β-Unsaturated Phosphine Sulfides

Xian-Liang Wang

^aDepartment of Chemistry, Shanghai University, 99 Shangda Road, Shanghai 200444, P. R. of China Email: xsjia@mail.shu.edu.cn

^bCAS Key Laboratory of Synthetic Chemistry of Natural Substances, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China Email: liangyin@sioc.ac.cn

,

Jin-Xiang Chen

^bCAS Key Laboratory of Synthetic Chemistry of Natural Substances, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China Email: liangyin@sioc.ac.cn

,

Xue-Shun Jia∗

^aDepartment of Chemistry, Shanghai University, 99 Shangda Road, Shanghai 200444, P. R. of China Email: xsjia@mail.shu.edu.cn

,

Liang Yin ∗

^bCAS Key Laboratory of Synthetic Chemistry of Natural Substances, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China Email: liangyin@sioc.ac.cn

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Abstract

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Abstract

α,β-Unsaturated phosphine sulfides may exhibit different reactivity from α,β-unsaturated phosphine oxides toward nucleophilic addition and thus may find new applications in copper(I)-catalyzed asymmetric reactions. Herein, various α,β-unsaturated phosphine sulfides were prepared in moderate to excellent yields from the parent α,β-unsaturated phosphine oxides with Lawesson’s reagent. The reaction enjoys a broad substrate scope and tolerates a variety of functional groups.

Key words

phosphine oxides - phosphine sulfides - thionation - Lawesson’s reagent - thiocarbonyl compounds

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References

References

For the ‘hard and soft acids and bases’ theory, see:

1a Pearson RG. J. Chem. Educ. 1968; 45: 581
1b Pearson RG. J. Chem. Educ. 1968; 45: 643

For some recent examples, see:

2a Iwata M, Yazaki R, Suzuki Y, Kumagai N, Shibasaki M. J. Am. Chem. Soc. 2009; 131: 18244
2b Iwata M, Yazaki R, Kumagai N, Shibasaki M. Tetrahedron: Asymmetry 2010; 21: 1688
2c Iwata M, Yazaki R, Chen I, Sureshkumar D, Kumagai N, Shibasaki M. J. Am. Chem. Soc. 2011; 133: 5554
2d Suzuki Y, Yazaki R, Kumagai N, Shibasaki M. Chem. Eur. J. 2011; 17: 11998
2e Kawato Y, Iwata M, Yazaki R, Kumagai N, Shibasaki M. Tetrahedron 2011; 67: 6539
2f Sureshkumar D, Kawato Y, Iwata M, Kumagai N, Shibasaki M. Org. Lett. 2012; 14: 3018
2g Suzuki Y, Iwata M, Yazaki R, Kumagai N, Shibasaki M. J. Org. Chem. 2012; 77: 4496
2h Gopinath P, Watanabe T, Shibasaki M. J. Org. Chem. 2012; 77: 9260
2i Kawato Y, Chaudhary S, Kumagai N, Shibasaki M. Chem. Eur. J. 2013; 19: 3802
2j Alagiri K, Lin S, Kumagai N, Shibasaki M. Org. Lett. 2014; 16: 5301
2k Matsuzawa A, Opie CR, Kumagai N, Shibasaki M. Chem. Eur. J. 2014; 20: 68
2l Bao Y, Kumagai N, Shibasaki M. Chem. Sci. 2015; 6: 6124
2m Cui J, Ohtsuki A, Watanabe T, Kumagai N, Shibasaki M. Chem. Eur. J. 2018; 24: 2598
2n Ota Y, Li Z, Kumagai N, Shibasaki M. Synlett 2019; 30: 620

For some recent examples, see:

3a Yazaki R, Kumagai N, Shibasaki M. J. Am. Chem. Soc. 2010; 132: 10275
3b Yanagida Y, Yazaki R, Kumagai N, Shibasaki M. Angew. Chem. Int. Ed. 2011; 50: 7910
3c Yazaki R, Kumagai N, Shibasaki M. Org. Lett. 2011; 13: 952
3d Yazaki R, Kumagai N, Shibasaki M. Chem. Asian J. 2011; 6: 1778
3e Ogawa T, Kumagai N, Shibasaki M. Angew. Chem. Int. Ed. 2012; 51: 8551
3f Ogawa T, Mouri S, Yazaki R, Kumagai N, Shibasaki M. Org. Lett. 2012; 14: 110
3g Yin L, Takada H, Lin S, Kumagai N, Shibasaki M. Angew. Chem. Int. Ed. 2014; 53: 5327
3h Majumdar N, Saito A, Yin L, Kumagai N, Shibasaki M. Org. Lett. 2015; 17: 3362

For the preparation of N-thiophosphinoyl ketimines, see:

4a Xu X, Wang C, Zhou Z, Zeng Z, Ma X, Zhao G, Tang C. Lett. Org. Chem. 2006; 3: 640
4b Xu X, Wang C, Zhou Z, Zeng Z, Ma X, Zhao G, Tang C. Heteroat. Chem. 2008; 19: 238

For some recent examples, see:

5a Yin L, Takada H, Kumagai N, Shibasaki M. Angew. Chem. Int. Ed. 2013; 52: 7310
5b Yin L, Otsuka Y, Takada H, Mouri S, Yazaki R, Kumagai N, Shibasaki M. Org. Lett. 2013; 15: 698
5c Yin L, Bao Y, Kumagai N, Shibasaki M. J. Am. Chem. Soc. 2013; 135: 10338
5d Lin S, Kawato Y, Kumagai N, Shibasaki M. Angew. Chem. Int. Ed. 2015; 54: 5183
5e Takada H, Kumagai N, Shibasaki M. Org. Lett. 2015; 17: 4762
5f Lin S, Kumagai N, Shibasaki M. Chem. Eur. J. 2016; 22: 3296
5g Lin S, Kumagai N, Shibasaki M. Org. Biomol. Chem. 2016; 14: 9725
5h Lin S, Otsuka Y, Yin L, Kumagai N, Shibasaki M. Org. Synth. 2017; 94: 313

6a Pedersen BS, Scheibye S, Nilsson NH, Lawesson S.-O. Bull. Soc. Chim. Belg. 1978; 87: 223
6b Scheibye S, Pedersen BS, Lawesson S.-O. Bull. Soc. Chim. Belg. 1978; 87: 229
6c Pedersen BS, Scheibye S, Clausen K, Lawesson S.-O. Bull. Soc. Chim. Belg. 1978; 87: 293
6d Fritz H, Hug P, Lawesson S.-O, Logemann E, Pedersen BS, Sauter H, Scheibye S, Winkler T. Bull. Soc. Chim. Belg. 1978; 87: 525

For reviews, see:

7a Cherkasov RA, Kutyrev GA, Pudovik AN. Tetrahedron 1985; 41: 2567
7b Cava MP, Levinson MI. Tetrahedron 1985; 41: 5061
7c Jesberger M, Davis TP, Barner L. Synthesis 2003; 1929
7d Ozturk T, Ertas E, Mert O. Chem. Rev. 2007; 107: 5210

For some selected examples, see:

8a Minetto G, Raveglia LF, Sega A, Taddei M. Eur. J. Org. Chem. 2005; 5277
8b Kaleta Z, Makowski BT, Soos T, Dembinski R. Org. Lett. 2006; 8: 1625
8c Seijas JA, Vázquez-Tato MP, Carballido-Reboredo MR, Crecente-Campo J, Romar-López L. Synlett 2007; 313
8d Sanz-Cervera JF, Blasco R, Piera J, Cynamon M, Ibáñez I, Murguía M, Fustero S. J. Org. Chem. 2009; 74: 8988
8e Giofrè SV, Romeo R, Mancuso R, Cicero N, Corriero N, Chiacchio U, Romeo G, Gabriele B. RSC Adv. 2016; 6: 20777

9a Rauchfuss TB, Zank GA. Tetrahedron Lett. 1986; 27: 3445
9b Yoshifuji M, An D.-L, Toyota K, Yasunami M. Tetrahedron Lett. 1994; 35: 4379

10a Legnani L, Toma L, Caramella P, Chiacchio MA, Giofrè S, Delso I, Tejero T, Merino P. J. Org. Chem. 2016; 81: 7733
10b Chiacchio MA, Legnani L, Caramella P, Tejero T, Merino P. Eur. J. Org. Chem. 2017; 1952
10c Mardyukov A, Niedek D, Schreiner PR. Chem. Commun. 2018; 54: 2715

For some selected examples, see:

11a Saeed A, Mehfooz H, Larik FA, Faisal M, Channar PA. J. Asian Nat. Prod. Res. 2017; 19: 1114
11b Mlostoń G, Hamera-Fałdyga R, Heimgartner H. Phosphorus, Sulfur Silicon Relat. Elem. 2017; 192: 732
11c Larik FA, Saeed A, Muqadar U, El-Seedi H, Faisal M, Channar PA, Mehfooz H. Phosphorus, Sulfur Silicon Relat. Elem. 2017; 192: 490
11d Mlostoń G, Hamera-Fałdyga R, Celeda M, Linden A, Heimgartner H. J. Sulfur Chem. 2017; 38: 475
11e Lashmanova EA, Kirdyashkina AI, Slepukhin PA, Shiryaev AK. Tetrahedron Lett. 2018; 59: 1099
11f Soleimani E, Robertson KN, Pye CC, Clyburne JA. C. Dalton Trans. 2018; 47: 6299

For some selected examples, see:

12a Kawashima T, Kojima S, Inamoto N. Chem. Lett. 1989; 849
12b McKenna CE, Ye T.-G, Levy JN, Pham P, Wen T, Bongartz J.-P, Starnes MC, Cheng Y.-C. Phosphorus, Sulfur Silicon Relat. Elem. 1990; 49/50: 183
12c Wen T, Bau R, McKenna CE. J. Chem. Soc., Chem. Commun. 1991; 1223
12d Zhou H.-J, Zhang Y.-Q, Li Y.-G, Wang J.-L, Liu X.-L, Miao F.-M, Yang S.-C, Jiang X.-C, Feng R, Yan Z.-X. Phosphorus, Sulfur Silicon Relat. Elem. 1995; 102: 185
12e Piettre SR, Raboisson P. Tetrahedron Lett. 1996; 37: 2229
12f Piettre SR. Tetrahedron Lett. 1996; 37: 4707
12g Zhou H.-J, Han J.-X, Li Y.-G, Ye T.-G, Wang J.-L, Miao F.-L. Phosphorus, Sulfur Silicon Relat. Elem. 1996; 112: 281
12h Polozov AM, Cremer SE, Fanwick PE. Can. J. Chem. 1999; 77: 1274
12i Lopin C, Gouhier G, Piettre SR. Tetrahedron Lett. 2003; 44: 8837
12j Tongcharoensirikul P, Suarez AI, Voelker T, Thompson CM. J. Org. Chem. 2004; 69: 2322
12k Chan JC.-H, Lam WH, Wong H.-L, Wong W.-T, Yam VW.-W. Angew. Chem. Int. Ed. 2013; 52: 11504

13 The application of the prepared α,β-unsaturated phosphine sulfides in copper(I)-catalyzed asymmetric reactions will be reported in due course.

14a Semenzin D, Etemad-Moghadam G, Albouy D, Diallo O, Koenig M. J. Org. Chem. 1997; 62: 2414
14b Parsons AF, Sharpe DJ, Taylor P. Synlett 2005; 2981
14c Artem’ev AV, Malysheva SF, Gusarova NK, Belogorlova NA, Shagun VA, Albanov AI, Trofimov BA. Synthesis 2015; 47: 263

15a Goli MB, Grim SO. Tetrahedron Lett. 1991; 32: 3631
15b Taillefer M, Cristau HJ. Tetrahedron Lett. 1998; 39: 7857
15c Taillefer M, Cristau HJ, Fruchier A, Vicente V. J. Organomet. Chem. 2001; 624: 307

16a Ohmiya H, Yorimitsu H, Oshima K. Angew. Chem. Int. Ed. 2005; 44: 2368
16b Perrier A, Comte V, Moïse C, Richard P, Gendre PL. Eur. J. Org. Chem. 2010; 1562
16c Moglie Y, González-Soria MJ, Martín-García I, Radivoy G, Alonso F. Green Chem. 2016; 18: 4896
16d Rajpurohit J, Kumar P, Shukla P, Shanmugam M, Shanmugam M. Organometallics 2018; 37: 2297

17a Niu M, Fu H, Jiang Y, Zhao Y. Chem. Commun. 2007; 272
17b Hornillos V, Vila C, Otten E, Feringa BL. Angew. Chem. Int. Ed. 2015; 54: 7867

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