A  meta ‐Selective C−H Alumination of Mono‐Substituted Benzene by Using An Alkyl‐Substituted Al Anion through Hydride‐Eliminating S N Ar Reaction | Zendy

Kurumada Satoshi | Zendy; Sugita Kengo | Zendy; Nakano Ryo | Zendy; Yamashita Makoto | Zendy

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A meta ‐Selective C−H Alumination of Mono‐Substituted Benzene by Using An Alkyl‐Substituted Al Anion through Hydride‐Eliminating S N Ar Reaction

Author(s) -

Kurumada Satoshi,

Sugita Kengo,

Nakano Ryo,

Yamashita Makoto

Publication year - 2020

Publication title -

angewandte chemie

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.202009138

Subject(s) - chemistry , toluene , selectivity , hydride , kinetic isotope effect , benzene , alkyl , ion , medicinal chemistry , reaction mechanism , photochemistry , organic chemistry , catalysis , deuterium , hydrogen , physics , quantum mechanics

Reaction of an Al‐centered anion with toluene proceeded to form C−H cleaved product with a perfect meta‐selectivity and a relatively small kinetic isotope effect (KIE, k H /k D =1.51). DFT calculations suggested a two‐step reaction mechanism and electronically controlled meta‐selectivity arising from the electron‐donating methyl group. The reaction with other mono‐substituted arenes was also investigated.

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