Rhodium catalysed dehydrogenative borylation of alkenes: Vinylboronates via C–H activation

Ibraheem A. I. Mkhalid, R.B. Coapes, S. Natasha Edes, D. Coventry, Fabio E. S. Souza, R.Ll. Thomas, Jonathan Hall, Siwei Bi, Zhenyang Lin, Todd B. Marder

Dalton Transactions · 2008 · 120 citations · 77 references

Concepts

Abstract

We present herein a high yield, highly selective catalytic synthesis of vinylboronate esters (VBEs), including 1,1-disubstituted VBEs, from alkenes without significant hydrogenation or hydroboration, using the simple catalyst precursor, trans-[RhCl(CO)(PPh3)2] (1), and the diboron reagents B2pin2 (2a, pin = pinacolato = OCMe2CMe2O) or B2neop2 (2b, neop = neopentylglycolato = OCH2CMe2CH2O), or the monoboron reagent HBpin, all of which are commercially available. The reactions were conducted at 80 degrees C using conventional heating, or in a microwave reactor at 150 degrees C.

References

77