Ru3(CO)12-Catalyzed Reaction of 1,6-Diynes, Carbon Monoxide, and Water via the Reductive Coupling of Carbon Monoxide

Cathleen M Crudden; Yuuki Maekawa; Joshua J Clarke; Tomohide Ida; Yoshiya Fukumoto; Naoto Chatani; Shinji Murai

doi:10.1021/acs.orglett.0c02349

Ru₃(CO)₁₂-Catalyzed Reaction of 1,6-Diynes, Carbon Monoxide, and Water via the Reductive Coupling of Carbon Monoxide

Org Lett. 2020 Nov 20;22(22):8747-8751. doi: 10.1021/acs.orglett.0c02349. Epub 2020 Aug 19.

Authors

Cathleen M Crudden^{1

2}, Yuuki Maekawa^{1

2}, Joshua J Clarke¹, Tomohide Ida³, Yoshiya Fukumoto³, Naoto Chatani³, Shinji Murai⁴

Affiliations

¹ Department of Chemistry, Queen's University, Chernoff Hall, Kingston, Ontario K7L 3N6, Canada.
² Institute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University, Chikusa, Nagoya 464-8601, Japan.
³ Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan.
⁴ Nara Institute of Science and Technology, Ikoma, Nara 630-0192, Japan.

PMID: 32812430
DOI: 10.1021/acs.orglett.0c02349

Abstract

We report the ruthenium-catalyzed cyclization of 1,6-diynes with two molecules of carbon monoxide and water to give a variety of catechols. This reaction likely proceeds through the intermediacy of the water-gas shift reaction to generate an yne-diol-type intermediate followed by a [4 + 2] cycloaddition with 1,6-diynes. The reaction requires no external reductants or hydride sources and provides a novel and valuable method for the synthesis of a variety of catechols.