Access to 2-Arylindoles via Decarboxylative C-C Coupling in Aqueous Medium and to Heteroaryl Carboxylates under Base-Free Conditions using Diaryliodonium Salts

Velladurai Arun; Meenakshi Pilania; Dalip Kumar

doi:10.1002/asia.201601290

Access to 2-Arylindoles via Decarboxylative C-C Coupling in Aqueous Medium and to Heteroaryl Carboxylates under Base-Free Conditions using Diaryliodonium Salts

Chem Asian J. 2016 Dec 6;11(23):3345-3349. doi: 10.1002/asia.201601290. Epub 2016 Nov 7.

Authors

Velladurai Arun¹, Meenakshi Pilania¹, Dalip Kumar¹

Affiliation

¹ Department of Chemistry, Birla Institute of Technology and Science, Pilani-, 333031, Rajasthan, India.

PMID: 27737502
DOI: 10.1002/asia.201601290

Abstract

Easily accessible heteroaromatic carboxylic acids and diaryliodonium salts were successfully employed to construct valuable 2-arylindoles and heteroaryl carboxylates in a regioselective fashion. C2-arylated indoles were produced using a Pd-catalyzed decarboxylative strategy in water without any base, oxidant, or ligand. Heteroaryl carboxylates were prepared under metal and base-free conditions. This protocol was successfully utilized to synthesize Paullone, a cyclin-dependent kinase (CDK) inhibitor.

Keywords: C−C coupling; arylation; diaryliodonium salt; heterocycles; homogeneous catalysis.