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Direct prenylation of aromatic and alpha,beta-unsaturated carboxamides via iridium-catalyzed C-H oxidative addition-allene insertion.

ABSTRACT: Exposure of aromatic carboxamides 1e-1m, heteroaromatic carboxamides 1n-1p, and alpha,beta-unsaturated carboxamides 1q-1s to 1,1-dimethylallene in the presence of the a cationic iridium complex derived from [Ir(cod)(2)]BAr(F)(4) and rac-BINAP results in direct C-H prenylation to furnish adducts 2e-2m, 2n-2p, and 2q-2s, respectively, in good isolated yields as single isomers.

SUBMITTER: Zhang YJ

PROVIDER: S-EPMC2858454 | biostudies-literature | 2009 Sep

REPOSITORIES: biostudies-literature

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Direct prenylation of aromatic and alpha,beta-unsaturated carboxamides via iridium-catalyzed C-H oxidative addition-allene insertion.

Zhang Yong Jian YJ Skucas Eduardas E Krische Michael J MJ

Organic letters 20090901 18

Exposure of aromatic carboxamides 1e-1m, heteroaromatic carboxamides 1n-1p, and alpha,beta-unsaturated carboxamides 1q-1s to 1,1-dimethylallene in the presence of the a cationic iridium complex derived from [Ir(cod)(2)]BAr(F)(4) and rac-BINAP results in direct C-H prenylation to furnish adducts 2e-2m, 2n-2p, and 2q-2s, respectively, in good isolated yields as single isomers. ...[more]

PMID: 19739691

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