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Solvent-controlled switchable C-H alkenylation of 4-aryl-1H-pyrrole-3-carboxylates: application to the total synthesis of (±)-rhazinilam. | LitMetric

Solvent-controlled switchable C-H alkenylation of 4-aryl-1H-pyrrole-3-carboxylates: application to the total synthesis of (±)-rhazinilam.

Org Lett

State Key Laboratory of Natural Medicines (SKLNM) and Department of Medicinal Chemistry, School of Pharmacy, China Pharmaceutical University, Nanjing, 210009, P. R. China.

Published: September 2014

A solvent-controlled switchable C-H alkenylation of 4-aryl-1H-pyrrole-3-carboxylates via a Pd(OAc)2 catalyzed oxidative Heck reaction was first realized. The corresponding C2 and C5 alkenylation products were obtained in good yields with high regioselectivities, respectively. The selective C5-alkenylation was successfully applied to the total synthesis of (±)-rhazinilam.

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http://dx.doi.org/10.1021/ol5023933DOI Listing

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