Room-Temperature Direct β-Arylation of Thiophenes and Benzo[b]thiophenes and Kinetic Evidence for a Heck-type Pathway

Research output: Contribution to journalArticle

  • Authors:
  • Chiara Colletto
  • Saidul Islam
  • Francisco Julia-Hernandez
  • Igor Larrosa

Abstract

The first example of a regioselective β-arylation of benzo[b]thiophenes and thiophenes at room temperature with aryl iodides as coupling partners is reported. This methodology stands out for its operational simplicity: no prefunctionalization of either starting material is required, the reaction is insensitive to air and moisture, and it proceeds at room temperature. The mild conditions afford wide functional group tolerance, often with complete regioselectivity and high yields, resulting in a highly efficient catalytic system. Initial mechanistic studies, including 13C and 2H KIEs, suggest that this process occurs via a concerted carbo-palladation across the thiophene double bond, followed by a base-assisted anti-elimination.

Bibliographical metadata

Original languageEnglish
Pages (from-to)1677-1683
Number of pages6
JournalAmerican Chemical Society. Journal
Volume138
Issue number5
DOIs
StatePublished - 2016