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Dehydrogenative B−H/C(sp 3 )−H Benzylic Borylation within the Coordination Sphere of Platinum(II)
Author(s) -
Kelly Colin M.,
Fuller Jack T.,
Macaulay Casper M.,
McDonald Robert,
Ferguson Michael J.,
Bischof Steven M.,
Sydora Orson L.,
Ess Daniel H.,
Stradiotto Mark,
Turculet Laura
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201700857
Subject(s) - borylation , chemistry , dehydrogenation , catalysis , metathesis , medicinal chemistry , platinum , coordination sphere , stoichiometry , stereochemistry , photochemistry , organic chemistry , ion , polymerization , alkyl , polymer , aryl
The first examples of stoichiometric dehydrogenative B−H/C(sp 3 )−H benzylic borylation reactions, which are of relevance to catalytic methylarene (di)borylation, are reported. These unusual transformations involving a (κ 2 ‐P,N)Pt(η 3 ‐benzyl) complex, and either pinacolborane or catecholborane, proceed cleanly at room temperature. Density functional calculations suggest that borylation occurs via successive σ‐bond metathesis steps, whereby a Pt II −H intermediate engages in C(sp 3 )−H bond activation‐induced dehydrogenation.