Synthesis 2015; 47(11): 1669-1677
DOI: 10.1055/s-0034-1380384
paper
© Georg Thieme Verlag Stuttgart · New York

Trifluoroborane-Catalyzed C–H Functionalization/S–H Insertion Reaction: Construction of N,S-Acetal Quaternary Centers

Yan Cai
a   State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. of China   Email: miaozhiwei@nankai.edu.cn
,
Haihong Ge
a   State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. of China   Email: miaozhiwei@nankai.edu.cn
,
Weize Sun
a   State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. of China   Email: miaozhiwei@nankai.edu.cn
,
Zhiwei Miao*
a   State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. of China   Email: miaozhiwei@nankai.edu.cn
b   Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071, P. R. of China
› Author Affiliations
Further Information

Publication History

Received: 31 October 2014

Accepted after revision: 19 February 2015

Publication Date:
25 March 2015 (online)


Abstract

The trifluoroborane-catalyzed C–H functionalization/S–H insertion reaction of α-diazophosphonates with thiols has been developed. A plausible reaction mechanism has been proposed to understand the combined reaction. This process provides straightforward access to N,S-acetals containing quaternary centers in moderate to good yields and chemoselectivity.

Supporting Information

 
  • References


    • For selected recent examples, see:
    • 1a DeLorbe JE, Jabri SY, Mennen SM, Overman LE, Zhang F.-L. J. Am. Chem. Soc. 2011; 133: 6549
    • 1b DeLorbe JE, Horne D, Jove R, Mennen SM, Nam S, Zhang F.-L, Overman LE. J. Am. Chem. Soc. 2013; 135: 4117
    • 1c Jabri SY, Overman LE. J. Am. Chem. Soc. 2013; 135: 4231
    • 1d Kim J, Ashenhurst JA, Movassaghi M. Science (Washington, D.C.) 2009; 324: 238
    • 1e Wang HY, Zhang JX, Cao DD, Zhao G. ACS Catal. 2013; 3: 2218
    • 2a Bull SD, Davies SG, Parkin RM, Sancho FS. J. Chem. Soc., Perkin Trans. 1 1998; 2313
    • 2b Ding G, Jiang L, Guo L, Chen X, Zhang H, Che Y. J. Nat. Prod. 2008; 71: 1861
    • 2c Kamei H, Oka M, Hamagishi Y, Tomita K, Komishi M, Oki T. J. Antibiot. 1990; 43: 1018
    • 2d Huang R, Zhou X, Xu T, Yang X, Liu Y. Chem. Biodiv. 2010; 7: 2809
    • 2e Cornacchia C, Cacciatore I, Baldassarre L, Mollica A, Feliciani F, Pinnen F. Mini-Rev. Med. Chem. 2012; 12: 2
    • 2f Borthwick AD. Chem. Rev. 2012; 112: 3641

      For selected epidithiodiketopiperazine total syntheses, see ref. 1a and:
    • 3a Williams RM, Rastetter WH. J. Org. Chem. 1980; 45: 2625
    • 3b Wu Z, Williams LJ, Danishefsky SJ. Angew. Chem. Int. Ed. 2000; 39: 3866
    • 3c Boyer N, Movassaghi M. Chem. Sci. 2012; 3: 1798
    • 3d Iwasa E, Hamashima Y, Fujishiro S, Higuchi E, Ito A, Yoshida M, Sodeoka M. J. Am. Chem. Soc. 2010; 132: 4078
    • 3e Kim J, Movassaghi M. J. Am. Chem. Soc. 2010; 132: 14376
    • 3f Fukuyama T, Nakatsuka S, Kishi Y. Tetrahedron 1981; 37: 2045
    • 3g Fukuyama T, Kishi Y. J. Am. Chem. Soc. 1976; 98: 6723

      For selected examples, see:
    • 4a Katritzky AR, Szajda M, Bayyuk S. Synthesis 1986; 804
    • 4b Kurz T, Widyan K, Elgemeie GH. Phosphorus, Sulfur Silicon Relat. Elem. 2006; 181: 299
    • 4c Kita Y, Shibata N, Kawano N, Yoshida N, Matsumoto K, Takebe Y. J. Chem. Soc., Perkin Trans. 1 1996; 2321

      For selected recent examples, see:
    • 5a Ingle GK, Mormino MG, Wojtas L, Antilla JC. Org. Lett. 2011; 13: 4822
    • 5b Fang X, Li Q.-H, Tao H.-Y, Wang C.-J. Adv. Synth. Catal. 2013; 355: 327
    • 5c Luo Z.-B, Hou X.-L, Dai L.-X. Tetrahedron: Asymmetry 2007; 18: 443
    • 5d Cao YM, Zhang FT, Shen FF, Wang R. Chem. Eur. J. 2013; 19: 9476
    • 6a Bartrun HE, Blakemore DC, Moody CJ, Hayes CJ. Tetrahedron 2013; 69: 2276
    • 6b Xu B, Zhu SF, Zhang ZC, Yu ZX, Ma Y, Zhou QL. Chem. Sci. 2014; 5: 1442

      For recent reviews, see:
    • 7a Xiao Q, Zhang Y, Wang JB. Acc. Chem. Res. 2013; 46: 236
    • 7b Zhao X, Zhang Y, Wang JB. Chem. Commun. 2012; 48: 10162
    • 7c Davies HM. L, Morton D. Chem. Soc. Rev. 2011; 40: 1857
    • 7d Doyle MP, Ratnikov M, Liu Y. Org. Biomol. Chem. 2011; 9: 4007
    • 7e Doyle MP, Duffy R, Ratnikov M, Zhou L, Ye T. Chem. Rev. 2010; 110: 704
    • 7f Zhang Y, Wang JB. Chem. Commun. 2009; 5350
    • 7g Padwa A. Chem. Soc. Rev. 2009; 38: 3072
    • 7h Davies HM. L, Denton JR. Chem. Soc. Rev. 2009; 38: 3061
    • 7i Zhang ZH, Wang JB. Tetrahedron 2008; 64: 6577
    • 7j Davies HM. L, Hedley SJ. Chem. Soc. Rev. 2007; 36: 1109
    • 7k Davies HM. L, Bechwith RE. J. Chem. Rev. 2003; 103: 2861
    • 7l Mckervey MA, Doyle MP, McKervey MA, Ye T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylide. Wiley; New York: 1998: 433-436
    • 7m Miller DJ. D, Moody J. Tetrahedron 1995; 51: 10811

      For elected examples on carbenoid C–H insertion, see ref. 7d and:
    • 8a DeAnglis A, Shurtleff VW, Dmitrenko O, Fox JM. J. Am. Chem. Soc. 2011; 133: 1650
    • 8b Wolckenhauser SA, Devlin AS, Du Bios J. Org. Lett. 2007; 9: 4363
    • 8c Davies HM. L. Angew. Chem. Int. Ed. 2006; 45: 6422
    • 8d Davies HM. L, Townsend RJ. J. Org. Chem. 2001; 66: 6595

    • For selected examples on carbenoid O–H insertion, see:
    • 8e Zhu SF, Song XG, Li Y, Cai Y, Zhou QL. J. Am. Chem. Soc. 2010; 132: 16374
    • 8f Zhu SF, Cha Y, Mao HX, Xie JH, Zhou QL. Nat. Chem. 2010; 2: 546
    • 8g Zhu SF, Chen C, Cai Y, Zhou QL. Angew. Chem. Int. Ed. 2008; 47: 932
    • 8h Chen C, Zhu SF, Liu B, Wang LX, Zhou QL. J. Am. Chem. Soc. 2007; 129: 12616
    • 8i Maier TC, Fu GC. J. Am. Chem. Soc. 2006; 128: 4594

    • For selected examples on carbenoid N–H insertion, see:
    • 8j Zhu SF, Xu B, Wang GP, Zhou QL. J. Am. Chem. Soc. 2012; 134: 436
    • 8k Hou ZR, Wang J, He P, Wang J, Qin B, Liu XH, Lin LL, Feng XM. Angew. Chem. Int. Ed. 2010; 49: 4763
    • 8l Liu B, Zhu SF, Zhang W, Chen C, Zhou QL. J. Am. Chem. Soc. 2007; 129: 5834
    • 8m Moody CJ. Angew. Chem. Int. Ed. 2007; 46: 9148

    • For selected examples on carbenoid Si–H insertion, see:
    • 8n Zhang YZ, Zhu SF, Wang LX, Zhou QL. Angew. Chem. Int. Ed. 2008; 47: 8496

      For metallo-carbene insertion into N–H bonds, see:
    • 9a Paulissen R, Hayez E, Hubert AJ, Teyssié P. Tetrahedron Lett. 1974; 15: 607
    • 9b Nicoud J.-F, Kagan H. Tetrahedron Lett. 1971; 12: 2065

    • For metallo-carbene insertion into O–H bonds, see:
    • 9c Cox GG, Miller DJ, Moody CJ, Sie E.-RH. B, Kulagowski JJ. Tetrahedron 1994; 50: 3195
    • 9d Haigh D. Tetrahedron 1994; 50: 3177
    • 9e Aller E, Cox GG, Miller DJ, Moody CJ. Tetrahedron Lett. 1994; 35: 5949
    • 9f Landais Y, Planchenault D. Synlett 1995; 1191
    • 9g Cox GG, Moody CJ, Austin DJ, Padwa A. Tetrahedron 1993; 49: 5109
    • 10a Moyer MP, Feldman PL, Rapoport H. J. Org. Chem. 1985; 50: 5223
    • 10b Brunner H, Wutz K, Doyle MP. Monatsh. Chem. 1990; 121: 755
    • 10c Bulugahapitiya P, Landais Y, Parra-Rapado L, Planchenault D, Weber V. J. Org. Chem. 1997; 62: 1630
  • 11 Zhang YZ, Zhu SF, Cai Y, Mao HX, Zhou QL. Chem. Commun. 2009; 5362
    • 12a Zhu SF, Chen WQ, Zhang QQ, Mao HX, Zhou QL. Synlett 2011; 919
    • 12b Zhou CY, Wang JC, Wei JH, Xu ZJ, Guo Z, Low KH, Che CM. Angew. Chem. Int. Ed. 2012; 51: 11376
    • 12c Briones JF, Davies HM. L. Org. Lett. 2011; 13: 3984
    • 12d Lindsay VN. G, Fiset D, Gritsch PJ, Azzi S, Charette AB. J. Am. Chem. Soc. 2013; 135: 1463
    • 12e Wang J, Boyarshikh V, Rainier JD. Org. Lett. 2011; 13: 700
    • 12f Davies HM. L, Lee GH. Org. Lett. 2004; 6: 2117
    • 12g Zhang H, Wen XJ, Gan LH, Peng YG. Org. Lett. 2012; 14: 2126
    • 12h Hashimoto T, Maruoka K. J. Am. Chem. Soc. 2007; 129: 10054
  • 13 Cai Y, Lu YC, Yu CB, Lyu HR, Miao ZW. Org. Biomol. Chem. 2013; 11: 5491

    • For recent reviews see the following:
    • 14a Palacios F, Alonso C, de los Santos JM. Chem. Rev. 2005; 105: 899
    • 14b Palacios F, Alonso C, de los Santos JM In Enantioselective Synthesis of β-Amino Acids . Juaristi E, Soloshonok VA. Wiley; New York: 2005. 2nd ed. 277-317
    • 15a Kong SS, Fan WD, Wu GP, Miao ZW. Angew. Chem. Int. Ed. 2012; 51: 8864
    • 15b Fang ZJ, Yang HH, Miao ZW, Chen RY. Helv. Chim. Acta 2011; 94: 1586
    • 15c Wang YD, Wang YY, Yu JP, Miao ZW, Chen RY. Chem. Eur. J. 2009; 15: 9290
    • 15d Wang YD, Wang F, Wang YY, Miao ZW, Chen RY. Adv. Synth. Catal. 2008; 350: 2339
    • 15e Cai Y, Lyu HR, Yu CB, Miao ZW. Adv. Synth. Catal. 2014; 356: 596
    • 16a Jiang N, Ma ZH, Qu ZH, Xing XY, Xie LF, Wang JB. J. Org. Chem. 2003; 68: 893
    • 16b Xiao FP, Zhang ZH, Zhang J, Wang JB. Tetrahedron Lett. 2005; 46: 8873
  • 17 See the supporting information for details on the crystal structure of 3f. Crystallographic data for the structural analysis of compound 3f has been deposited at the Cambridge Crystallographic Data Centre as No. CCDC 969832. These data can be obtained free of charge by contacting The Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033; E-mail: deposit@ccdc.cam.ac.uk.
  • 18 Cai Y, Ge HH, Yu CB, Sun WZ, Zhan JC, Miao ZW. RSC Adv. 2014; 4: 21492