2.6 C—C Bond Formation by C—H Carboxylation or Carbonylation

Abstract

The direct C—H carbonylation or carboxylation involving carbon monoxide is an ideal and environmentally friendly method toward the synthesis of carboxylic acids and derivatives. Within this emerging area, a number of significant examples have been reported, which are summarized in this chapter. Additionally, the recent progress on C—H carboxylation utilizing carbon dioxide is included in this review.

Schlüsselwörter

C—H carbonylation - C—H carboxylation - carbon monoxide - carbon dioxide - directing groups - transition-metal catalysis - carboxylic acids - carboxylic esters - carboxylic amides - carbonyl compounds

• 1 Schoenberg A, Bartoletti I, Heck RF. J. Org. Chem. 1974; 39: 3318

• 2 Schoenberg A, Heck RF. J. Org. Chem. 1974; 39: 3327

• 3 Brennführer A, Neumann H, Beller M. Angew. Chem. Int. Ed. 2009; 48: 4114

• 4 Wu X.-F, Neumann H, Beller M. Chem. Rev. 2013; 113: 1

• 5 Wu X.-F, Neumann H, Beller M. Chem. Soc. Rev. 2011; 40: 4986

• 6 Liu Q, Li G, He J, Liu J, Li P, Lei A. Angew. Chem. Int. Ed. 2010; 49: 3371

• 7 Zhao Y, Jin L, Li P, Lei A. J. Am. Chem. Soc. 2008; 130: 9429

• 8 Liu Q, Zhang H, Lei A. Angew. Chem. Int. Ed. 2011; 50: 10788

• 9 Gabriele B, Mancuso R, Salerno G. Eur. J. Org. Chem. 2012; 6825

• 10 Gabriele B, Salerno G, Costa M. Top. Organomet. Chem. 2006; 18: 239

• 11 Fujiwara Y, Takaki K, Taniguchi Y. Synlett 1996; 591

• 12 Ackermann L. Angew. Chem. Int. Ed. 2011; 50: 3842

• 13 Cokoja M, Bruckmeier C, Rieger B, Herrmann WA, Kühn FE. Angew. Chem. Int. Ed. 2011; 50: 8510

• 14 Sakakura T, Choi J.-C, Yasuda H. Chem. Rev. 2007; 107: 2365

• 15 Huang K, Sun C.-L, Shi Z.-J. Chem. Soc. Rev. 2011; 40: 2435

• 16 Ohashi S, Sakaguchi S, Ishii Y. Chem. Commun. (Cambridge) 2005; 486

• 17 Giri R, Yu J.-Q. J. Am. Chem. Soc. 2008; 130: 14082

• 18 Giri R, Lam JK, Yu J.-Q. J. Am. Chem. Soc. 2010; 132: 686

• 19 Dai H.-X, Stepan AF, Plummer MS, Zhang Y.-H, Yu J.-Q. J. Am. Chem. Soc. 2011; 133: 7222

• 20 Boogaerts IIF, Nolan SP. J. Am. Chem. Soc. 2010; 132: 8858

• 21 Boogaerts IIF, Fortman GC, Furst MRL, Cazin CSJ, Nolan SP. Angew. Chem. Int. Ed. 2010; 49: 8674

• 22 Zhang L, Cheng J, Ohishi T, Hou Z. Angew. Chem. Int. Ed. 2010; 49: 8670

• 23 Mizuno H, Takaya J, Iwasawa N. J. Am. Chem. Soc. 2011; 133: 1251

• 24 Zhang H, Shi R, Gan P, Liu C, Ding A, Wang Q, Lei A. Angew. Chem. Int. Ed. 2012; 51: 5204

• 25 Orito K, Horibata A, Nakamura T, Ushito H, Nagasaki H, Yuguchi M, Yamashita S, Tokuda M. J. Am. Chem. Soc. 2004; 126: 14342

• 26 Wada Y, Nagasaki H, Tokuda M, Orito K. J. Org. Chem. 2007; 72: 2008

• 27 Haffemayer B, Gulias M, Gaunt MJ. Chem. Sci. 2011; 2: 312

• 28 López B, Rodriguez A, Santos D, Albert J, Ariza X, Garcia J, Granell J. Chem. Commun. (Cambridge) 2011; 47: 1054

• 29 Liang D, Hu Z, Peng J, Huang J, Zhu Q. Chem. Commun. (Cambridge) 2013; 49: 173

• 30 Rajeshkumar V, Lee T.-H, Chuang S.-C. Org. Lett. 2013; 15: 1468

• 31 Lu Y, Leow D, Wang X, Engle KM, Yu J.-Q. Chem. Sci. 2011; 2: 967

• 32 Inoue S, Shiota H, Fukumoto Y, Chatani N. J. Am. Chem. Soc. 2009; 131: 6898

• 33 Shibata K, Hasegawa N, Fukumoto Y, Chatani N. ChemCatChem 2012; 4: 1733

• 34 Wrigglesworth JW, Cox B, Lloyd-Jones GC, Booker-Milburn KI. Org. Lett. 2011; 13: 5326

• 35 Du Y, Hyster TK, Rovis T. Chem. Commun. (Cambridge) 2011; 47: 12074

• 36 Guan Z.-H, Chen M, Ren Z.-H. J. Am. Chem. Soc. 2012; 134: 17490

• 37 Ma B, Wang Y, Peng J, Zhu Q. J. Org. Chem. 2011; 76: 6362

• 38 Zhang H, Liu D, Chen C, Liu C, Lei A. Chem.–Eur. J. 2011; 17: 9581

• 39 Lang R, Wu J, Shi L, Xia C, Li F. Chem. Commun. (Cambridge) 2011; 47: 12553

• 40 Guan Z.-H, Ren Z.-H, Spinella SM, Yu S, Liang Y.-M, Zhang X. J. Am. Chem. Soc. 2009; 131: 729

• 41 Houlden CE, Hutchby M, Bailey CD, Ford JG, Tyler SNG, Gagné MR, Lloyd-Jones GC, Booker-Milburn KI. Angew. Chem. Int. Ed. 2009; 48: 1830

• 42 Li H, Cai G.-X, Shi Z.-J. Dalton Trans. 2010; 39: 10442

• 43 Yoo EJ, Wasa M, Yu J.-Q. J. Am. Chem. Soc. 2010; 132: 17378

• 44 Hasegawa N, Charra V, Inoue S, Fukumoto Y, Chatani N. J. Am. Chem. Soc. 2011; 133: 8070

• 45 Xie P, Xie Y, Qian B, Zhou H, Xia C, Huang H. J. Am. Chem. Soc. 2012; 134: 9902