A Tandem Approach to Functionalized Carbazoles from Indoles via Two Successive Regioselective Oxidative Heck Reactions Followed by Thermal Electrocyclization

Joydev K Laha; Neetu Dayal

doi:10.1021/acs.orglett.5b02265

A Tandem Approach to Functionalized Carbazoles from Indoles via Two Successive Regioselective Oxidative Heck Reactions Followed by Thermal Electrocyclization

Org Lett. 2015 Oct 2;17(19):4742-5. doi: 10.1021/acs.orglett.5b02265.

Authors

Joydev K Laha¹, Neetu Dayal¹

Affiliation

¹ Department of Pharmaceutical Technology (Process Chemistry), National Institute of Pharmaceutical Education and Research , S. A. S. Nagar, Punjab 160062, India.

PMID: 26402033
DOI: 10.1021/acs.orglett.5b02265

Abstract

A direct one-pot approach to the synthesis of carbazoles (mono-, di-, and trisubstituted) and α-carbolines from readily available indoles or 7-azaindoles and alkenes is described. Based on mechanistic studies, the tandem reaction follows the sequence: palladium-catalyzed regioselective C-3 alkenylation/palladium-catalyzed C-2 alkenylation/thermal electrocyclization.

Publication types

Research Support, Non-U.S. Gov't