1.4.4 Catalytic Boron Addition Reactions

Abstract

The use of N-heterocyclic carbenes (NHCs) in metal-mediated and metal-free catalytic borylation reactions is described. Special emphasis is given to the activation mode of the borane reagent by a metal–NHC complex or an NHC itself, as well as its influence on the delivery of the boryl moiety onto unsaturated substrates to generate a C—B bond efficiently and selectively. Asymmetric induction can be achieved in borylation reactions using chiral N-heterocyclic carbenes and a detailed range of examples is highlighted.

Key words

N-heterocyclic carbenes - borylation - C—B bonds - selectivity - hydroboration - diboration - carboboration - alkenes - alkynes - carbonyl compounds - imines

• 1 Boronic Acids: Preparation and Applications in Organic Synthesis, Medicine and Materials. Hall DG. Wiley-VCH; Weinheim, Germany 2011

• 2 Synthesis and Applications of Organoboron Compounds. Fernández E, Whiting A. Springer; Heidelberg 2015

• 3 Ramírez J, Corberán R, Sanaú M, Peris E, Fernández E. Chem. Commun. (Cambridge) 2005; 3056

• 4 Laitar DS, Müller P, Sadighi JP. J. Am. Chem. Soc. 2005; 127: 17196

• 5 Corberán R, Ramírez J, Poyatos M, Peris E, Fernández E. Tetrahedron: Asymmetry 2006; 17: 1759

• 6 Laitar DS, Tsui EY, Sadighi JP. Organometallics 2006; 25: 2405

• 7 Laitar DS, Tsui EY, Sadighi JP. J. Am. Chem. Soc. 2006; 128: 11036

• 8 Dang L, Zhao H, Lin Z, Marder TB. Organometallics 2007; 26: 2824

• 9 Lillo V, Fructos MR, Ramírez J, Braga AAC, Maseras F, Díaz-Requejo MM, Pérez PJ, Fernández E. Chem.–Eur. J. 2007; 13: 2614

• 10 Marder TB. Organomet. Chem. 2008; 34: 46

• 11 Dang L, Lin Z, Marder TB. Chem. Commun. (Cambridge) 2009; 3987

• 12 Cid J, Gulyás H, Carbó JJ, Fernández E. Chem. Soc. Rev. 2012; 41: 3558

• 13 Lee Y, Hoveyda AH. J. Am. Chem. Soc. 2009; 131: 3160

• 14 Corberán R, Mszar NW, Hoveyda AH. Angew. Chem. Int. Ed. 2011; 50: 7079

• 15 Ondrusek BA, Opalka SM, Hietsoi O, Shatruk M, McQuade DT. Synlett 2013; 24: 1211

• 16 Jang H, Zhugralin AR, Lee Y, Hoveyda AH. J. Am. Chem. Soc. 2011; 133: 7859

• 17 Yoshida H, Kageyuki I, Takaki K. Org. Lett. 2014; 16: 3512

• 18 Kim HR, Jung IG, Yoo K, Jang K, Lee ES, Yun J, Son SU. Chem. Commun. (Cambridge) 2010; 46: 758

• 19 Semba K, Fujihara T, Terao J, Tsuji Y. Chem.–Eur. J. 2012; 18: 4179

• 20 Fujihara T, Semba K, Terao J, Tsuji Y. Catal. Sci. Technol. 2014; 4: 1699

• 21 Park JK, Ondrusek BA, McQuade DT. Org. Lett. 2012; 14: 4790

• 22 Bidal YD, Lazreg F, Cazin CSJ. ACS Catal. 2014; 4: 1564

• 23 Lillo V, Prieto A, Bonet A, Díaz-Requejo MM, Ramírez J, Pérez PJ, Fernández E. Organometallics 2009; 28: 659

• 24 OʼBrien JM, Lee K.-s, Hoveyda AH. J. Am. Chem. Soc. 2010; 132: 10630

• 25 Hirsch-Weil D, Abboud KA, Hong S. Chem. Commun. (Cambridge) 2010; 46: 7525

• 26 Niu Z, Chen J, Chen Z, Ma M, Song C, Ma Y. J. Org. Chem. 2015; 80: 602

• 27 Zhao L, Ma Y, He F, Duan W, Chen J, Song C. J. Org. Chem. 2013; 78: 1677

• 28 Hong B, Ma Y, Zhao L, Duan W, He F, Song C. Tetrahedron: Asymmetry 2011; 22: 1055

• 29 Park JK, Lackey HH, Rexford MD, Kovnir K, Shatruk M, McQuade DT. Org. Lett. 2010; 12: 5008

• 30 Huang L, Cao Y, Zhao M, Tang Z, Sun Z. Org. Biomol. Chem. 2014; 12: 6554

• 31 He Z.-T, Zhao Y.-S, Tian P, Wang C.-C, Dong H.-Q, Lin G.-Q. Org. Lett. 2014; 16: 1426

• 32 Iwai T, Akiyama Y, Sawamura M. Tetrahedron: Asymmetry 2013; 24: 729

• 33 Lee K.-s, Zhugralin AR, Hoveyda AH. J. Am. Chem. Soc. 2009; 131: 7253

• 34 Gao M, Thorpe SB, Kleeberg C, Slebodnick C, Marder TB, Santos WL. J. Org. Chem. 2011; 76: 3997

• 35 Pietsch S, Neeve EC, Apperley DC, Bertermann R, Mo F, Qiu D, Cheung MS, Dang L, Wang J, Radius U, Lin Z, Kleeberg C, Marder TB. Chem.–Eur. J. 2015; 21: 7082

• 36 Dewhurst RD, Neeve EC, Braunschweig H, Marder TB. Chem. Commun. (Cambridge) 2015; 51: 9594

• 37 Wu H, Radomkit S, OʼBrien JM, Hoveyda AH. J. Am. Chem. Soc. 2012; 134: 8277

• 38 Radomkit S, Hoveyda AH. Angew. Chem. Int. Ed. 2014; 53: 3387

• 39 Hartmann E, Vyas DJ, Oestreich M. Chem. Commun. (Cambridge) 2011; 47: 7917

• 40 Takaya J, Iwasawa N. ACS Catal. 2012; 2: 1993

• 41 Dang L, Zhao H, Lin Z, Marder TB. Organometallics 2008; 27: 1178

• 42 Corberán R, Lillo V, Mata JA, Fernández E, Peris E. Organometallics 2007; 26: 4350

• 43 Lillo V, Mas-Marzá E, Segarra AM, Carbó JJ, Bo C, Peris E, Fernández E. Chem. Commun. (Cambridge) 2007; 3380

• 44 Lee Y, Jang H, Hoveyda AH. J. Am. Chem. Soc. 2009; 131: 18234

• 45 Zhao H, Dang L, Marder TB, Lin Z. J. Am. Chem. Soc. 2008; 130: 5586

• 46 McIntosh ML, Moore CM, Clark TB. Org. Lett. 2010; 12: 1996

• 47 Vogels CM, Westcott SA. Curr. Org. Chem. 2005; 9: 687

• 48 Endo K, Hirokami M, Shibata T. Synlett 2009; 1331

• 49 Beenen MA, An C, Ellman JA. J. Am. Chem. Soc. 2008; 130: 6910

• 50 Zhang S.-S, Zhao Y.-S, Tian P, Lin G.-Q. Synlett 2013; 24: 437

• 51 Suginome M. Chem. Rec. 2010; 10: 348

• 52 Suginome M, Yamamoto A, Murakami M. J. Am. Chem. Soc. 2003; 125: 6358

• 53 Daini M, Yamamoto A, Suginome M. J. Am. Chem. Soc. 2008; 130: 2918

• 54 Zhang L, Cheng J, Carry B, Hou Z. J. Am. Chem. Soc. 2012; 134: 14314

• 55 Yoshida H, Kageyuki I, Takaki K. Org. Lett. 2013; 15: 952

• 56 Semba K, Nakao Y. J. Am. Chem. Soc. 2014; 136: 7567

• 57 Smith KB, Logan KM, You W, Brown MK. Chem.–Eur. J. 2014; 20: 12032

• 58 Logan KM, Smith KB, Brown MK. Angew. Chem. Int. Ed. 2015; 54: 5228

• 59 Meng F, Jang H, Jung B, Hoveyda AH. Angew. Chem. Int. Ed. 2013; 52: 5046

• 60 Zhou Y, You W, Smith KB, Brown MK. Angew. Chem. Int. Ed. 2014; 53: 3475