Synthesis 2016; 48(17): 2816-2822
DOI: 10.1055/s-0035-1560439
special topic
© Georg Thieme Verlag Stuttgart · New York

Nickel-Catalyzed Reductive Carboxylation of Cyclopropyl Motifs with Carbon Dioxide

Toni Moragas
a   Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007 Tarragona, Catalonia, Spain
,
Ruben Martin*
a   Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007 Tarragona, Catalonia, Spain
b   Catalan Institution for Research and Advanced Studies (ICREA), Passeig Lluïs Companys 23, 08010 Barcelona, Catalonia, Spain   eMail: rmartinromo@iciq.es
› Institutsangaben
Weitere Informationen

Publikationsverlauf

Received: 09. März 2016

Accepted: 13. März 2016

Publikationsdatum:
11. April 2016 (online)


Abstract

A nickel-catalyzed reductive carboxylation technique for the synthesis of cyclopropanecarboxylic acids has been developed. This user-friendly and mild transformation operates at atmospheric pressure of carbon dioxide and utilizes either organic halides or alkene precursors, thus representing the first example of catalytic reductive carboxylation of secondary counterparts lacking adjacent π-components.

Supporting Information

Primary Data

 
  • References

    • 1a Gu J, Wang X, Xue W, Gong H. Org. Chem. Front. 2015; 2: 1411
    • 1b Weix JD. Acc. Chem. Res. 2015; 48: 1767
    • 1c Moragas T, Correa A, Martin R. Chem. Eur. J. 2014; 20: 8242
    • 1d Tasker SZ, Standley EA, Jamison TF. Nature 2014; 509: 299
    • 1e Knappke CE. I, Grupe S, Gärtner D, Corpet M, Gosmini C, Jacobi von Wangelin A. Chem. Eur. J. 2014; 20: 6828

      For selected reviews, see:
    • 2a Zhang L, Hou Z. Chem. Sci. 2013; 4: 3395
    • 2b Tsuji Y, Fujihara T. Chem. Commun. 2012; 48: 9956
    • 2c Cokoja M, Bruckmeier C, Rieger B, Herrmann WA, Kuhn FE. Angew. Chem. Int. Ed. 2011; 50: 8510
    • 2d Huang K, Sun C.-L, Shi Z.-J. Chem. Soc. Rev. 2011; 40: 2435
    • 2e Martin R, Kleij AW. ChemSusChem 2011; 4: 1259
    • 2f Sakakura T, Choi JC, Yasuda H. Chem. Rev. 2007; 107: 2365
    • 3a Patai S. The Chemistry of Acid Derivatives . Wiley; New York: 1992
    • 3b Gooßen LJ, Rodríguez N, Gooßen K. Angew. Chem. Int. Ed. 2008; 47: 3100
    • 3c Maag H. Prodrugs of Carboxylic Acids . Springer; New York: 2007
  • 4 Osakada K, Sato R, Yamamoto T. Organometallics 1994; 13: 4645
    • 5a Wang X, Nakajima M, Martin R. J. Am. Chem. Soc. 2015; 137: 8924
    • 5b Wang X, Liu Y, Martin R. J. Am. Chem. Soc. 2015; 137: 6476
    • 5c Moragas T, Cornella J, Martin R. J. Am. Chem. Soc. 2014; 136: 17702
    • 5d Liu Y, Cornella J, Martin R. J. Am. Chem. Soc. 2014; 136: 11212
    • 5e Correa A, León T, Martin R. J. Am. Chem. Soc. 2014; 136: 1062
    • 5f León T, Correa A, Martin R. J. Am. Chem. Soc. 2013; 135: 1221
    • 5g Correa A, Martin R. J. Am. Chem. Soc. 2009; 131: 15974
    • 6a Nogi K, Fujihara T, Terao J, Tsuji Y. J. Org. Chem. 2015; 80: 11618
    • 6b Rebih F, Andreini M, Moncomble A, Harrison-Marchand A, Maddaluno J, Durandetti M. Chem. Eur. J. 2016; 22: 3758
    • 6c Mita T, Higuchi Y, Sato Y. Chem. Eur. J. 2015; 21: 16391
    • 6d Nogi K, Fujihara T, Terao J, Tsuji Y. Chem. Commun. 2014; 50: 13052
    • 6e Tran-Vu H, Daugulis O. ACS Catal. 2013; 3: 2417
    • 6f Fujihara T, Nogi K, Xu T, Terao J, Tsuji Y. J. Am. Chem. Soc. 2012; 134: 9106
  • 7 Exner K, von Ragué Schleyer P. J. Phys. Chem. A 2001; 105: 3407 ; and references cited therein
    • 8a Lemonier G, Lion C, Quirion J.-C, Pin J.-P, Goudet C, Jubault P. Bioorg. Med. Chem. 2012; 20: 4716
    • 8b Reichelt A, Martin SF. Acc. Chem. Res. 2006; 39: 433
    • 8c Mohapatra DK, Datta A. J. Org. Chem. 1998; 63: 642
    • 8d Martin SF, Austin RE, Oalman CJ, Baker WR, Condon SL, deLara E, Rosenberg SH, Spina KP, Stein HH, Cohen J, Kleinert HD. J. Med. Chem. 1992; 35: 1710
    • 9a Alper H. Isr. J. Chem. 1981; 21: 203
    • 9b Yu M, Pagenkopf BL. Tetrahedron 2005; 61: 321
    • 9c Volger HC, Hogeveen H, Gaasbeek MM. P. J. Am. Chem. Soc. 1969; 91: 2137
    • 10a Ahrens T, Kohlmann J, Ahrens M, Braun T. Chem. Rev. 2015; 115: 931
    • 10b Cornella J, Zarate C, Martin R. Chem. Soc. Rev. 2014; 43: 8081
    • 10c Arendt K, Doyle AG. Angew. Chem. Int. Ed. 2015; 54: 9876
  • 11 Rubin M, Rubina M, Gevorgyan V. Chem. Rev. 2007; 107: 3117 ; and references cited therein
  • 12 Fischer R, Langer J, Malassa A, Walther D, Görls H, Vaughan G. Chem. Commun. 2006; 2510
  • 13 Recently, nickel(I) species have been shown to rapidly react with CO2; see: Menges FS, Craig SM, Tötsch N, Bloomfield A, Ghosh S, Krüger H.-J, Johnson MA. Angew. Chem. Int. Ed. 2016; 55: 1282
  • 14 For an example of a carboxylation of an organomanganese species with CO2, see: Friour G, Cahiez G, Alexakis A, Normant JF. Bull. Soc. Chim. Fr. 1979; 515
    • 15a Hou J, Xie J.-H, Hou Q.-L. Angew. Chem. Int. Ed. 2015; 54: 6302
    • 15b Li S, Yuan W, Ma S. Angew. Chem. Int. Ed. 2011; 50: 2578
    • 15c Fujihara T, Xu T, Semba K, Terao J, Tsuji T. Angew. Chem. Int. Ed. 2011; 50: 523
    • 15d See also refs. 5a and 5b.

      For selected examples of nickel hydride intermediates with silanes, see:
    • 16a Buslov I, Becouse J, Mazza S, Montandon-Clerc M, Hu X. Angew. Chem. Int. Ed. 2015; 54: 14523
    • 16b Wu S, Li X, Xiong Z, Xu W, Lu Y, Sun H. Organometallics 2013; 32: 3227
    • 16c Cornella J, Gomez-Bengoa E, Martin R. J. Am. Chem. Soc. 2013; 135: 1997
    • 16d Tobisu M, Yamakawa K, Shimasaki T, Chatani N. Chem. Commun. 2011; 47: 2946
    • 16e Alvarez-Bercedo P, Martin R. J. Am. Chem. Soc. 2010; 132: 17353
    • 16f Tanabe M, Yumoto R, Osakada K. Chem. Commun. 2012; 48: 2125
    • 17a See ref. 12.
    • 17b Hoberg H, Peres Y, Krüger C, Tsay YH. Angew. Chem., Int. Ed. Engl. 1987; 26: 771
    • 17c Hoberg H, Schaefer D, Burkhardt G, Krüger C, Romão MJ. J. Organomet. Chem. 1984; 266: 203
    • 17d Hoberg H, Schaefer D. J. Organomet. Chem. 1983; 251: c51
    • 17e Burkhardt G, Hoberg H. Angew. Chem., Int. Ed. Engl. 1982; 21: 76
  • 18 For an example of a transmetalation reaction, see: Ohashi M, Kishizaki O, Ikeda H, Ogoshi S. J. Am. Chem. Soc. 2009; 131: 9160
  • 19 Alberti MN, Orfanopoulos M. Org. Lett. 2008; 10: 2465
  • 20 O’Brien EM, Bercot EA, Rovis T. J. Am. Chem. Soc. 2003; 125: 10498
  • 21 Concellón JM, Rodríguez-Solla H, Simal C. Org. Lett. 2007; 9: 2685
  • 22 Jiang Y, Chen C.-A, Lu K, Daniewska I, De Leon J, Kong R, Forray C, Li B, Hegde LG, Wolinsky TD, Craig DA, Wetzel JM, Andersen K, Marzabadi MR. J. Med. Chem. 2007; 50: 3870