BArF3-catalyzed imine hydroboration with pinacolborane not requiring the assistance of an additional Lewis base

Yin, Qin, Soltani, Yashar, Melen, Rebecca ORCID: https://orcid.org/0000-0003-3142-2831 and Oestreich, Martin 2017. BArF3-catalyzed imine hydroboration with pinacolborane not requiring the assistance of an additional Lewis base. Organometallics 36 (13) , pp. 2381-2384. 10.1021/acs.organomet.7b00381

Preview

PDF - Accepted Post-Print Version Download (656kB) | Preview

Abstract

The rarely used boron Lewis acid tris[3,5- bis(trifluoromethyl)phenyl]borane (BArF 3) is found to be an excellent catalyst for metal-free hydroboration of imines. In the presence of 1.0 mol % of BArF 3, several ketimines and aldimines undergo hydroboration with pinacolborane (HBpin) at room temperature without the aid of an external Lewis base. BArF 3 is more reactive than other Lewis-acidic boranes, including often-used tris(pentafluorophenyl)borane [B(C6F5)3]. The steric hindrance imparted by the six fluorine atoms ortho to the boron center in B(C6F5)3 accounts for this. Mechanistic control experiments indicate conventional Lewis-acid catalysis involving imine activation and hydride transfer from HBpin.

Item Type:	Article
Date Type:	Published Online
Status:	Published
Schools:	Chemistry
Subjects:	Q Science > QD Chemistry
Publisher:	American Chemical Society
ISSN:	0276-7333
Date of First Compliant Deposit:	18 July 2017
Date of Acceptance:	15 June 2017
Last Modified:	06 Nov 2023 19:26
URI:	https://orca.cardiff.ac.uk/id/eprint/102526

Citation Data

Cited 65 times in Scopus. View in Scopus. Powered By Scopus® Data

Actions (repository staff only)

Edit Item