Synthesis 2014; 46(14): 1901-1907
DOI: 10.1055/s-0033-1339111
special topic
© Georg Thieme Verlag Stuttgart · New York

Nickel-Catalyzed Reductive Allylation of Ketones with Allylic Carbonates

Chenglong Zhao
a   Department of Chemistry, Shanghai University, 99 Shang-Da Road, Shanghai 200444, P. R. of China   Fax: +86(21)66132410   Email: wdeng@shu.edu.cn   Email: Hegui_gong@shu.edu.cn
,
Zhuozhen Tan
a   Department of Chemistry, Shanghai University, 99 Shang-Da Road, Shanghai 200444, P. R. of China   Fax: +86(21)66132410   Email: wdeng@shu.edu.cn   Email: Hegui_gong@shu.edu.cn
,
Zhuye Liang
b   College of Chemistry and Molecular Engineering, Zhengzhou University, 100 Science Road, Zhengzhou 450001, P. R. of China
,
Wei Deng*
a   Department of Chemistry, Shanghai University, 99 Shang-Da Road, Shanghai 200444, P. R. of China   Fax: +86(21)66132410   Email: wdeng@shu.edu.cn   Email: Hegui_gong@shu.edu.cn
,
Hegui Gong*
a   Department of Chemistry, Shanghai University, 99 Shang-Da Road, Shanghai 200444, P. R. of China   Fax: +86(21)66132410   Email: wdeng@shu.edu.cn   Email: Hegui_gong@shu.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 12 March 2014

Accepted after revision: 13 April 2014

Publication Date:
28 May 2014 (online)


Abstract

Nickel-catalyzed efficient umpolung allylation of ketones with allylic carbonates in the presence of zinc powder is developed, which accommodates a variety of allylic and ketone substrates. Although chiral ligand is necessary for the transformation, no enantioselectivity was observed.

Supporting Information

 
  • References


    • For reviews on enantioselective carbonyl allylation, see:
    • 1a Yus M, González-Gómez JC, Foubelo F. Chem. Rev. 2011; 111: 7774
    • 1b Marek I, Sklute G. Chem. Commun. 2007; 1683
    • 1c Hall DG. Synlett 2007; 1644
    • 1d Denmark SE, Fu J. Chem. Rev. 2003; 103: 2763
    • 1e Kennedy JW. J, Hall DG. Angew. Chem. Int. Ed. 2003; 42: 4732
    • 1f Ramachandran PV. Aldrichimica Acta 2002; 35: 23

      For selected examples of asymmetric NHK reactions, see:
    • 2a Xia G, Yamamoto H. J. Am. Chem. Soc. 2006; 128: 2554
    • 2b Deng Q.-H, Wadepohl H, Gade LH. Chem. Eur. J. 2011; 17: 14922
    • 2c Bandini M, Cozzi PG, Melchiorre P, Umani-Ronchi A. Angew. Chem. Int. Ed. 1999; 38: 3357
    • 2d Zhang Z, Aubry S, Kishi Y. Org. Lett. 2011; 13: 3077
    • 2e Guo H, Dong C.-G, Kim D.-S, Urabe D, Wang J, Kim JT, Liu X, Sasaki T, Kishi Y. J. Am. Chem. Soc. 2009; 131: 15387
    • 2f Berkessel A, Menche D, Sklorz CA, Schroder M, Paterson I. Angew. Chem. Int. Ed. 2003; 42: 1032

      For selected examples of asymmetric Barbier reactions, see:
    • 4a Haddad TD, Hirayama LC, Singaram B. J. Org. Chem. 2010; 75: 642
    • 4b Hirayama LC, Gamsey S, Knueppel D, Steiner D, Dela Torre K, Singaram B. Tetrahedron Lett. 2005; 46: 2315

      For nonasymmetric coupling of allylic alcohol/thioether with carbonyl compounds using Rh/B, see:
    • 5a Williams FJ, Grote RE, Jarvo ER. Chem. Commun. 2012; 48: 1496

    • Rh/CO:
    • 5b Vasylyev M, Alper H. J. Org. Chem. 2010; 75: 2710

      For Ru/CO, see:
    • 6a Denmark SE, Nguyen ST. Org. Lett. 2009; 11: 781

    • For Ru-catalzyed reactions involving secondary alcohols, see:
    • 6b McInturff EL, Nguyen KD, Krische MJ. Angew. Chem. Int. Ed. 2014; 53, 3232
    • 6c McInturff EL, Mowat J, Waldeck AR, Krische MJ. J. Am. Chem. Soc. 2013; 135: 17230
    • 6d Park BY, Montgomery TP, Garza V, Krische MJ. J. Am. Chem. Soc. 2013; 135, 16320
    • 6e Yamaguchi E, Mowat J, Luong T, Krische MJ. Angew. Chem. Int. Ed. 2013; 52: 8428
  • 7 For nonasymmetric allylation using [Ir(cod)Cl]2/SnCl2, see: Roy S, Banerjee M. J. Mol. Catal. A 2006; 246: 231

    • For iridium-catalyzed transfer hydrogenation, see:
    • 8a Dechert-Schmitt A.-MR, Schmitt DC, Krische MJ. Angew. Chem. Int. Ed. 2013; 52: 3195
    • 8b Kim I.-S, Ngai M.-Y, Krische MJ. J. Am. Chem. Soc. 2008; 130: 6340
    • 8c Kim IS, Ngai M-Y, Krische MJ. J. Am. Chem. Soc. 2008; 130: 14891

    • Allyliridium/alcohol:
    • 8d Bower JF, Skucas E, Patman RL, Krische MJ. J. Am. Chem. Soc. 2007; 129: 15134

      For selected examples of palladium-catalyzed nonasymmetric carbonyl allylation with allylic alcohols and acetates, see: Pd/Et2Zn:
    • 9a Flahaut A, Toutah K, Mangeney P, Roland S. Eur. J. Inorg. Chem. 2009; 5422
    • 9b Kimura M, Shimizu M, Shibata K, Tazoe M, Tamaru Y. Angew. Chem. Int. Ed. 2003; 42: 3392

    • Pd(OAc)2/Et3B:
    • 9c Kimura M, Tomizawa T, Horino Y, Tanaka S, Tamaru Y. Tetrahedron Lett. 2000; 41: 3627

    • Pd/diboron via allyl–B:
    • 9d Selander N, Kipke A, Sebelius S, Szabó KJ. J. Am. Chem. Soc. 2007; 129: 13723

    • Pd/SmI2:
    • 9e Jacquet O, Bergholz T, Magnier-Bouvier C, Mellah M, Guillot R, Fiaud J.-C. Tetrahedron 2010; 66: 222

      Palladium-catalyzed asymmetric umpolung using Pd/Et2Zn:
    • 10a Zanoni G, Gladiali S, Marchetti A, Piccinini P, Tredici I, Vidari G. Angew. Chem. Int. Ed. 2004; 43: 846

    • Pd/B:
    • 10b Zhu S.-F, Qiao X.-C, Zhang Y.-Z, Wang L.-X, Zhou Q.-L. Chem. Sci. 2011; 2: 1135
    • 10c Zhu SF, Yang Y, Wang L.-X, Liu B, Zhou Q.-L. Org. Lett. 2005; 7: 2333
  • 11 Co/Zn: Gomes P, Gosmini C, Périchon J. Synthesis 2003; 1909

    • Iron-electrochemical reduction:
    • 12a Durandetti M, Meignein C, Périchon J. J. Org. Chem. 2003; 68: 3121

    • Fe/Mn:
    • 12b Muriel DM, Périchon J. Tetrahedron Lett. 2006; 47: 6255

      For nonasymmetric coupling of allylic alcohol/thioether with carbonyl compounds using titanium-mediated protocols modulated by nickel or palladium, see:
    • 13a Campaa AG, Bazdi B, Fuentes N, Robles R, Cuerva JM, Oltra JE, Porcel S, Echavarren AM. Angew. Chem. Int. Ed. 2008; 47: 7515

    • Ti:
    • 13b Takeda T, Yamamoto M, Yoshida S, Tsubouchi M. Angew. Chem. Int. Ed. 2012; 51: 7263

      For nonasymmetric carbonyl allylation with allyl-OR under Ni/InI, see:
    • 14a Hirashita T, Kambe S, Tsuji H, Omori H, Araki S. J. Org. Chem. 2004; 69: 5054

    • Intramolecular coupling of allyl ether with aldehyde:
    • 14b Franco D, Wenger K, Antonczak S, Cabrol-Bass D, Dunach E, Rocamora M, Gomez M, Muller G. Chem. Eur. J. 2002;  8:  664
    • 15a Montgomery J. Angew. Chem. Int. Ed. 2004; 43: 3890
    • 15b Köpfer A, Sam B, Breit B, Krische MJ. Chem. Sci. 2013; 4: 1876
    • 16a Dai Y, Wu F, Zang Z, You H, Gong H. Chem. Eur. J. 2012; 16: 808
    • 16b Tan Z, Wan X, Zang Z, Qian Q, Deng W, Gong H. Chem. Commun. 2014; 50: 3827

      For stoichiometric addition of allyl–Ni(I) to carbonyl, see:
    • 17a Corey EJ, Semmelhack MF. J. Am. Chem. Soc. 1967; 89: 2755
    • 17b Hegedus LS, Stiverson RK. J. Am. Chem. Soc. 1974; 96: 3250
    • 18a For reductive transmetalation of allylpalladium with indium, see: Fontana G, Lubineau A, Scherrmann M.-C. Org. Biomol. Chem. 2005; 3: 1375

    • Possible transmetalation of allylnickel with zinc:
    • 18b Durandetti S, Sibille S, Perichon J. J. Org. Chem. 1989; 54: 2198
  • 19 For Barbier-type allylation involving addition of allylzinc to carbonyl, see: Berton BW, Shugart JH, Hughey CA, Conrad BP, Perala SM. Molecules 2001; 6: 655