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“Inverse” Frustrated Lewis Pairs: An Inverse FLP Approach to the Catalytic Metal Free Hydrogenation of Ketones
Author(s) -
Mummadi Suresh,
Brar Amandeep,
Wang Guoqiang,
Kenefake Dustin,
Diaz Rony,
Unruh Daniel K.,
Li Shuhua,
Krempner Clemens
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201804370
Subject(s) - frustrated lewis pair , inverse , catalysis , catalytic hydrogenation , combinatorics , chemistry , computational chemistry , mathematics , lewis acids and bases , organic chemistry , geometry
For the first time have boron‐containing weak Lewis acids been demonstrated to be active components of Frustrated Lewis Pair (FLP) catalysts in the hydrogenation of ketones to alcohols. Combining the organosuperbase (pyrr) 3 P=N t Bu with the Lewis acid 9‐(4‐CF 3 ‐C 6 H 4 )‐BBN generated an “inverse” FLP catalyst capable of hydrogenating a range of aliphatic and aromatic ketones including N‐, O‐ and S‐functionalized substrates and bio‐mass derived ethyl levulinate. Initial computational and experimental studies indicate the mechanism of catalytic hydrogenation with “inverse” FLPs to be different from conventional FLP catalysts that contain strong Lewis acids such as B(C 6 F 5 ) 3 .