Catalytic Dehydrogenative Cyclization of o-Teraryls under pH-Neutral and Oxidant-Free Conditions
Corresponding Author
Tatsuhiro Tsukamoto
Department of Chemistry, University of Chicago, Chicago, IL, 60637 USA
Search for more papers by this authorCorresponding Author
Guangbin Dong
Department of Chemistry, University of Chicago, Chicago, IL, 60637 USA
Search for more papers by this authorCorresponding Author
Tatsuhiro Tsukamoto
Department of Chemistry, University of Chicago, Chicago, IL, 60637 USA
Search for more papers by this authorCorresponding Author
Guangbin Dong
Department of Chemistry, University of Chicago, Chicago, IL, 60637 USA
Search for more papers by this authorDedicated to Professor Eiichi Nakamura on the occasion of his 70th birthday
Abstract
A cobaloxime-catalyzed acceptorless dehydrogenative cyclization of o-teraryls was developed. In stark contrast to the established methods such as the Scholl or Mallory reactions, this method does not require any strong acids or oxidants, and shows high atom economy and a broad substrate scope. It operates at near room temperature with light as the source of energy. Acid- or oxidant-sensitive functional groups, such as 4-methoxyphenyl, unprotected benzyl alcohol, silyl ether, and thiophene groups are tolerated. Remarkably, aryls with electron-withdrawing groups, and electron-poor heteroarenes, such as pyridine and pyrimidine, can also react. Preliminary mechanistic study reveals that hydrogen gas is released during the reaction, and both light and the cobalt catalyst are important for the dehydrogenation step.
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