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Frustrated Lewis Pair Mediated Csp 3 −H Activation
Author(s) -
Rochette Étienne,
Courtemanche MarcAndré,
Fontaine FrédéricGeorges
Publication year - 2017
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.201700390
Subject(s) - frustrated lewis pair , chemistry , hydride , cleavage (geology) , nitrogen atom , aryl , molecule , stereochemistry , bond cleavage , lewis acids and bases , crystallography , group (periodic table) , catalysis , materials science , organic chemistry , hydrogen , alkyl , composite material , fracture (geology)
The cleavage of a Csp 3 −H bond by an N/B frustrated Lewis pair (FLP) is reported. Upon mild heating, the ambiphilic molecule (2‐NMe 2 ‐C 6 H 4 ) 2 BH activates the C−H bond of a methyl group in α position of a nitrogen atom to generate an unprecedented N–B heterocycle. Upon further heating, the novel species rearranges through a hydride abstraction/1,2‐aryl shift sequence. The mechanistic details of these transformations are investigated by quantum mechanical calculations.
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