Palladium‐Catalysed Regioselective Direct Arylations of Heteroarenes by Bromobenzamides: Direct Synthesis of Heteroaryl Benzamides

doi:10.1002/cctc.201200867

Paper

Palladium‐Catalysed Regioselective Direct Arylations of Heteroarenes by Bromobenzamides: Direct Synthesis of Heteroaryl Benzamides

Published Jul 1, 2013 · Lujun Chen, C. Bruneau, P. Dixneuf

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Abstract

The Pd‐catalysed direct arylation of heteroarene CH bonds by 2‐ or 4‐bromobenzamides has been achieved. In the presence of KOAc as the base, no CN bond formation or CC coupling of two bromobenzamides was observed. Both primary and tertiary amides can be employed for CC cross‐coupling of 4‐bromobenzamides with a variety of heteroarenes to give the C5‐arylated heteroarenes in good yields by using a low loading (0.5 mol %) of Pd(OAc)2 catalyst. However, no coupling product was observed with 2‐bromobenzamide, and a moderate reactivity of 2‐bromo‐N,N‐diethylbenzamide has been observed with 2 mol % PdCl(C3H5)(dppb) (dppb=1,4‐bis(diphenylphosphino)butane) as the catalyst. A moderate influence due to the nature of the heteroarene was observed, and thiazoles, thiophenes, furans and pyrroles have been arylated successfully. The reaction of a thiazole with 2‐bromo‐N‐phenylbenzamide led to a six‐membered ring product by intramolecular cyclisation, whereas a 2‐bromo‐N‐benzylbenzamide gave the desired intermolecular coupling product.

Study Snapshot

Pd-catalyzed direct arylation of heteroarene C-H bonds by bromobenzamides allows for the synthesis of C5-arylated heteroarenes in good yields, with moderate influence due to the heteroarene's nature.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Palladium‐Catalysed Regioselective Direct Arylations of Heteroarenes by Bromobenzamides: Direct Synthesis of Heteroaryl Benzamides

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