Ru3(CO)12-Catalyzed Reaction of 1,6-Diynes, Carbon Monoxide, and Water via the Reductive Coupling of Carbon Monoxide
Author(s) -
Cathleen M. Crudden,
Yuuki Maekawa,
Joshua J. Clarke,
Tomohide Ida,
Yoshiya Fukumoto,
Naoto Chatani,
Shinji Murai
Publication year - 2020
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.0c02349
Subject(s) - carbon monoxide , chemistry , catalysis , ruthenium , water gas shift reaction , hydride , cycloaddition , molecule , coupling reaction , diol , photochemistry , organic chemistry , hydrogen
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.
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