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
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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: | 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: | 03 Dec 2024 23:30 |
| URI: | https://orca.cardiff.ac.uk/id/eprint/102526 |
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