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. 2016 Dec 15:12:2757-2762.
doi: 10.3762/bjoc.12.272. eCollection 2016.

Direct arylation catalysis with chloro[8-(dimesitylboryl)quinoline-κN]copper(I)

Sem Raj Tamang  1 , James D Hoefelmeyer  1
Affiliations

Direct arylation catalysis with chloro[8-(dimesitylboryl)quinoline-κN]copper(I)

Sem Raj Tamang et al. Beilstein J Org Chem. .

Abstract

We report direct arylation of arylhalides with unactivated sp2 C-H bonds in benzene and naphthalene using a copper(I) catalyst featuring an ambiphilic ligand, (quinolin-8-yl)dimesitylborane. Direct arylation could be achieved with 0.2 mol % catalyst and 3 equivalents of base (KO(t-Bu)) at 80 °C to afford TON ≈160-190 over 40 hours.

Keywords: C–C coupling; C–H activation; catalysis; copper; direct arylation.

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Figures

Scheme 1
Scheme 1
Coordination of Cu(I) with the ambiphilic ligand 1 to form the catalyst 2.
Scheme 2
Scheme 2
Proposed mechanism of direct arylation catalyzed by 2 (X = Cl/I; Ar = aryl).
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