2.12 C—B Bond Formation by Arene C—H Activation

Abstract

This chapter provides a survey of the most useful available methodologies for the direct borylation of arenes and hetarenes, which proceed in all cases via a C—H activation event mediated by transition metals such as rhodium, iridium, or palladium. The borylation reactions have been organized into two main groups: (1) direct borylations with regioselectivity mainly controlled by steric factors, and (2) site-selective borylation, with regioselectivity driven by directing effects.

Schlüsselwörter

C—H activation - organoboron compounds - borylation - arenes - hetarenes - synthetic methods - rhodium - iridium - palladium - directing groups

• 1 Iverson CN, Smith III MR. J. Am. Chem. Soc. 1999; 121: 7696

• 2 Chen H, Hartwig JF. Angew. Chem. 1999; 111: 3597 Angew. Chem. Int. Ed. 1999; 38: 3391

• 3 Mkhalid IAI, Barnard JH, Marder TB, Murphy JM, Hartwig JF. Chem. Rev. 2010; 110: 890

• 4 Hartwig JF. Acc. Chem. Res. 2012; 45: 864

• 5 Ros A, Fernández R, Lassaletta JM. Chem. Soc. Rev. 2014; 43: 3229

• 6 Chen H, Schlecht S, Semple TC, Hartwig JF. Science (Washington, D. C.) 2000; 287: 1995

• 7 Cho J.-Y, Iverson CN, Smith III MR. J. Am. Chem. Soc. 2000; 122: 12868

• 8 Tse MK, Cho J.-Y, Smith III MR. Org. Lett. 2001; 3: 2831

• 9 Cho J.-Y, Tse MK, Holmes D, Maleczka Jr RE, Smith III MR. Science (Washington, D. C.) 2002; 295: 305

• 10 Ishiyama T, Takagi J, Ishida K, Miyaura N, Anastasi NR, Hartwig JF. J. Am. Chem. Soc. 2002; 124: 390

• 11 Ishiyama T, Takagi J, Hartwig JF, Miyaura N. Angew. Chem. 2002; 114: 3182 Angew. Chem. Int. Ed. 2002; 41: 3056

• 12 Takagi J, Sato K, Hartwig JF, Ishiyama T, Miyaura N. Tetrahedron Lett. 2002; 43: 5649

• 13 Ishiyama T, Takagi J, Yonekawa Y, Hartwig JF, Miyaura N. Adv. Synth. Catal. 2003; 345: 1103

• 14 Ishiyama T, Nobuta Y, Hartwig JF, Miyaura N. Chem. Commun. (Cambridge) 2003; 2924

• 15 Kikuchi T, Nobuta Y, Umeda J, Yamamoto Y, Ishiyama T, Miyaura N. Tetrahedron 2008; 64: 4967

• 16 Robbins DW, Hartwig JF. Org. Lett. 2012; 14: 4266

• 17 Robbins DW, Hartwig JF. Angew. Chem. 2013; 125: 967 Angew. Chem. Int. Ed. 2013; 52: 933

• 18 Shi F, Smith III MR, Maleczka Jr RE. Org. Lett. 2006; 8: 1411

• 19 Tzschucke CC, Murphy JM, Hartwig JF. Org. Lett. 2007; 9: 761

• 20 Murphy JM, Liao X, Hartwig JF. J. Am. Chem. Soc. 2007; 129: 15434

• 21 Partridge BM, Hartwig JF. Org. Lett. 2013; 15: 140

• 22 Liskey CW, Liao X, Hartwig JF. J. Am. Chem. Soc. 2010; 132: 11389

• 23 Liu T, Shao X, Wu Y, Shen Q. Angew. Chem. 2012; 124: 555 Angew. Chem. Int. Ed. 2012; 51: 540

• 24 Chotana GA, Rak MA, Smith III MR. J. Am. Chem. Soc. 2005; 127: 10539

• 25 Preshlock SM, Ghaffari B, Maligres PE, Krska SW, Maleczka Jr RE, Smith III MR. J. Am. Chem. Soc. 2013; 135: 7572

• 26 Ishiyama T, Isou H, Kikuchi T, Miyaura N. Chem. Commun. (Cambridge) 2010; 46: 159

• 27 Itoh H, Kikuchi T, Ishiyama T, Miyaura N. Chem. Lett. 2011; 40: 1007

• 28 Kawamorita S, Ohmiya H, Hara K, Fukuoka A, Sawamura M. J. Am. Chem. Soc. 2009; 131: 5058

• 29 Yamazaki K, Kawamorita S, Ohmiya H, Sawamura M. Org. Lett. 2010; 12: 3978

• 30 Kawamorita S, Ohmiya H, Sawamura M. J. Org. Chem. 2010; 75: 3855

• 31 Ros A, Estepa B, López-Rodríguez R, Álvarez E, Fernández R, Lassaletta JM. Angew. Chem. 2011; 123: 11928 Angew. Chem. Int. Ed. 2011; 50: 11724

• 32 Ros A, López-Rodríguez R, Estepa B, Álvarez E, Fernández R, Lassaletta JM. J. Am. Chem. Soc. 2012; 134: 4573

• 33 López-Rodríguez R, Ros A, Fernández R, Lassaletta JM. J. Org. Chem. 2012; 77: 9915

• 34 Roering AJ, Hale LVA, Squier PA, Ringgold MA, Wiederspan ER, Clark TB. Org. Lett. 2012; 14: 3558

• 35 Konishi S, Kawamorita S, Iwai T, Steel PG, Marder TB, Sawamura M. Chem.–Asian J. 2014; 9: 434

• 36 Kawamorita S, Miyazaki T, Ohmiya H, Iwai T, Sawamura M. J. Am. Chem. Soc. 2011; 133: 19310

• 37 Jiang Q, Duan-Mu D, Zhong W, Chen H, Yan H. Chem.–Eur. J. 2013; 19: 1903

• 38 Dai H.-X, Yu J.-Q. J. Am. Chem. Soc. 2012; 134: 134

• 39 Xiao B, Li Y.-M, Liu Z.-J, Yang H.-Y, Fu Y. Chem. Commun. (Cambridge) 2012; 48: 4854

• 40 Kuninobu Y, Iwanaga T, Omura T, Takai K. Angew. Chem. 2013; 125: 4527 Angew. Chem. Int. Ed. 2013; 52: 4431

• 41 Fernández-Salas JA, Manzini S, Piola L, Slawin AMZ, Nolan SP. Chem. Commun. (Cambridge) 2014; 50: 6782

• 42 Boebel TA, Hartwig JF. J. Am. Chem. Soc. 2008; 130: 7534

• 43 Robbins DW, Boebel TA, Hartwig JF. J. Am. Chem. Soc. 2010; 132: 4068

• 44 Roosen PC, Kallepalli VA, Chattopadhyay B, Singleton DA, Maleczka Jr RE, Smith III MR. J. Am. Chem. Soc. 2012; 134: 11350

• 45 Paul S, Chotana GA, Holmes D, Reichle RC, Maleczka Jr RE, Smith III MR. J. Am. Chem. Soc. 2006; 128: 15552

• 46 Preshlock SM, Plattner DL, Maligres PE, Krska SW, Maleczka Jr RE, Smith III MR. Angew. Chem. 2013; 125: 13153 Angew. Chem. Int. Ed. 2013; 52: 12915

• 47 Hatanaka T, Ohki Y, Tatsumi K. Chem.–Asian J. 2010; 5: 1657