Selective Catalytic Synthesis of α-Alkylated Ketones and β-Disubstituted Ketones via Acceptorless Dehydrogenative Cross-Coupling of Alcohols

Dipanjan Bhattacharyya; Bikash Kumar Sarmah; Sekhar Nandi; Hemant Kumar Srivastava; Animesh Das

doi:10.1021/acs.orglett.0c04098

Selective Catalytic Synthesis of α-Alkylated Ketones and β-Disubstituted Ketones via Acceptorless Dehydrogenative Cross-Coupling of Alcohols

Org Lett. 2021 Feb 5;23(3):869-875. doi: 10.1021/acs.orglett.0c04098. Epub 2021 Jan 21.

Authors

Dipanjan Bhattacharyya¹, Bikash Kumar Sarmah¹, Sekhar Nandi¹, Hemant Kumar Srivastava², Animesh Das¹

Affiliations

¹ Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, Assam, India.
² Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research Guwahati, Guwahati 781101, Assam, India.

PMID: 33476162
DOI: 10.1021/acs.orglett.0c04098

Abstract

Herein, a phosphine-free pincer ruthenium(III) catalyzed β-alkylation of secondary alcohols with primary alcohols to α-alkylated ketones and two different secondary alcohols to β-branched ketones are reported. Notably, this transformation is environmentally benign and atom efficient with H₂O and H₂ gas as the only byproducts. The protocol is extended to gram-scale reaction and for functionalization of complex vitamin E and cholesterol derivatives.