Regioselective C-H Alkenylation and Unsymmetrical Bis-olefination of Heteroarene Carboxylic Acids with Ruthenium Catalysis in Water

Anup Mandal, Ratnadeep Bera, Mahiuddin Baidya

Research output: Contribution to journalArticlepeer-review

14 Scopus citations

Abstract

An efficient weak carboxylate-assisted oxidative cross-dehydrogenative C-H/C-H coupling (CDC) of heteroarenes with readily available olefins has been devised employing water as green solvent under ruthenium(II) catalysis. The reaction is operationally simple, accommodates a large variety of heteroaromatic carboxylic acids as well as olefins, and facilitates a diverse array of high-value olefin-tethered heteroarenes in high yields (up to 87%). The potential of this ortho-C-H bond activation strategy has also been exploited toward tunable synthesis of densely functionalized heteroarenes through challenging unsymmetrical bis-olefination process in a one-pot sequential fashion. Mechanistic investigation demonstrates a reversible ruthenation process and C-H metalation step might not be involved in the rate-determining step.

Original languageEnglish
Pages (from-to)62-73
Number of pages12
JournalJournal of Organic Chemistry
Volume86
Issue number1
DOIs
StatePublished - 1 Jan 2021
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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