Bis(pinacolato)diboron

Introduction

Bis(pinacolato)diboron (B₂pin_2, Figure [1, ]CAS: 73183-34-3) is an air-stable, odourless, colorless powder that is commercially available. Being a major tool for the introduction of boron atoms into organic compounds, it is widely known as a good reagent to prepare substrates for the Suzuki–Miyaura reaction.

An extensive scope of reactions, including C–H activation of C(sp²) –H and C(sp³) –H bonds,[ ¹ ] borylation of α,β-unsaturated derivatives and substitutions of allylic carbonates, have been recently described in the literature. Over the past few years, extensive efforts have been devoted to the borylation of dienes, allenes,[ ² ] alkenes,[ ³ ] and alkynes. More recently, B₂pin₂ found application in the borylation of aldehydes and imines opening new ways of ­research.

Borylated products, obtained from these new strategies, could successfully be used in oxidation, allylation or ­coupling reactions.

Figure 1

• References

• 1a Maleczka RE, Shi F, Holmes D, Smith MR. J. Am. Chem. Soc. 2003; 125: 7792
• 1b Murphy JM, Tzschucke CC, Hartwig JF. Org. Lett. 2007; 9: 757
• 2a Pelz NF, Woodward AR, Burks HE, Sieber JD, Morken JP. J. Am. Chem. Soc. 2004; 126: 16328
• 2b Yuan W, Ma S. Adv. Synth. Catal. 2012; 354: 1867
• 3 Cho HY, Yu Z, Morken JP. Org. Lett. 2011; 13: 5267
• 4 Kawamorita S, Miyazaki T, Iwai T, Ohmiya H, Sawamura M. J. Am. Chem. Soc. 2012; 134: 12924
• 5 Ito H, Kawakami C, Sawamura M. J. Am. Chem. Soc. 2005; 127: 16034
• 6 Ito H, Ito S, Sasaki Y, Matsuura K, Sawamura M. J. Am. Chem. Soc. 2007; 129: 14856
• 7 Laitar DS, Tsui EY, Sadighi JP. J. Am. Chem. Soc. 2006; 128: 11036
• 8 Beenen MA, An C, Ellman JA. J. Am. Chem. Soc. 2008; 130: 6910
• 9 Solé C, Gulyás H, Fernandez E. Chem. Commun. 2012; 48: 3769
• 10 Selander N, Szabó K. J. Org. Chem. 2009; 74: 5695
• 11 Jang H, Zhugralin AR, Lee Y, Hoveyda AH. J. Am. Chem. Soc. 2011; 133: 7859
• 12 Joshi-Pangu A, Ma X, Diane M, Iqbal D, Kribs RJ, Huang R, Wang C-Y, Biscoe MR. J. Org. Chem. 2012; 77: 6629
• 13a Lee J, Yun J. Angew. Chem. Int. Ed. 2008; 47: 145
• 13b O’Brien JM, Lee K, Hoveyda AH. J. Am. Chem. Soc. 2010; 132: 10630
• 13c Lee JCh. H, McDonald R, Hall DG. Nat. Chem. 2011; 3: 894
• 14 Chea H, Sim H, Yun J. Adv. Synth. Catal. 2009; 351: 855
• 15a Chen I, Yin L, Itano W, Kanai M, Shibasaki M. J. Am. Chem. Soc. 2009; 131: 11664
• 15b Wu H, Radomkit S, O'Brien JM, Hoveyda AH. J. Am. Chem. Soc. 2012; 134: 8277