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

Yin, Qin, Soltani, Yashar, Melen, Rebecca 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

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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: 20 Oct 2019 14:01
URI: http://orca-mwe.cf.ac.uk/id/eprint/102526

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