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An efficient computational model to predict the synthetic utility of heterocyclic arynes.

ABSTRACT: Think before you act: a computational approach is reported for evaluating the synthetic potential of heterocyclic arynes. Routine and rapid calculations of arene dehydrogenation energies and aryne angle distortion predict the likelihood that a given hetaryne can be generated, as well as the degree of regioselectivity expected in a reaction between a given hetaryne and a nucleophilic trapping agent.

SUBMITTER: Goetz AE

PROVIDER: S-EPMC4502420 | biostudies-literature | 2012 Mar

REPOSITORIES: biostudies-literature

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An efficient computational model to predict the synthetic utility of heterocyclic arynes.

Goetz Adam E AE Bronner Sarah M SM Cisneros Jordan D JD Melamed Joshua M JM Paton Robert S RS Houk K N KN Garg Neil K NK

Angewandte Chemie (International ed. in English) 20120203 11

Think before you act: a computational approach is reported for evaluating the synthetic potential of heterocyclic arynes. Routine and rapid calculations of arene dehydrogenation energies and aryne angle distortion predict the likelihood that a given hetaryne can be generated, as well as the degree of regioselectivity expected in a reaction between a given hetaryne and a nucleophilic trapping agent. ...[more]

PMID: 22307724

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