Dehydrogenative B−H/C(sp 3 )−H Benzylic Borylation within the Coordination Sphere of Platinum(II) | Zendy

Kelly Colin M. | Zendy; Fuller Jack T. | Zendy; Macaulay Casper M. | Zendy; McDonald Robert | Zendy; Ferguson Michael J. | Zendy; Bischof Steven M. | Zendy; Sydora Orson L. | Zendy; Ess Daniel H. | Zendy; Stradiotto Mark | Zendy; Turculet Laura | Zendy

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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

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201700857

Subject(s) - borylation , chemistry , dehydrogenation , metathesis , catalysis , platinum , medicinal chemistry , coordination sphere , stoichiometry , stereochemistry , crystallography , organic chemistry , polymerization , crystal structure , 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.

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