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 2020; 52(01): 141-149
DOI: 10.1055/s-0039-1690685
DOI: 10.1055/s-0039-1690685
paper
Synthesis of α,β-Unsaturated Phosphine Sulfides
We gratefully acknowledge the financial support from the ‘Thousand Youth Talents Plan’, the National Natural Science Foundation of China (No. 21672235 and No. 21871287), the Strategic Priority Research Program of the Chinese Academy of Sciences (No. XDB20000000), the CAS Key Laboratory of Synthetic Chemistry of Natural Substances, and the Shanghai Institute of Organic Chemistry.Further Information
Publication History
Received: 26 July 2019
Accepted after revision: 05 September 2019
Publication Date:
30 September 2019 (online)
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 compoundsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690685.
- Supporting Information
-
References
- 1a Pearson RG. J. Chem. Educ. 1968; 45: 581
- 1b Pearson RG. J. Chem. Educ. 1968; 45: 643
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
For the ‘hard and soft acids and bases’ theory, see:
For some recent examples, see:
For some recent examples, see:
For the preparation of N-thiophosphinoyl ketimines, see:
For some recent examples, see:
For reviews, see:
For some selected examples, see:
For some selected examples, see:
For some selected examples, see: