Catalytic Formation of α-Aryl Ketones by C-H Functionalization with Cyclic Alkenyl Carbonates and One-Pot Synthesis of Isocoumarins.

Org Lett

Department of Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan and.

Published: October 2015


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Article Abstract

We report here a method for direct catalytic introduction of simple α-acylalkyl groups via rhodium-catalyzed C-H functionalization with cyclic alkenyl carbonates, synthetic equivalents to enolates bearing leaving groups. The reaction proceeded smoothly without using bases to give α-aryl ketones in high yields. Various nitrogen-containing aromatic rings and amide groups serve as directing groups. 3-Substituted isocoumarins can also be prepared by one-pot C-H functionalization/cyclization.

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http://dx.doi.org/10.1021/acs.orglett.5b02414DOI Listing

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