4.8 Article

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

Journal

ORGANIC LETTERS
Volume 17, Issue 19, Pages 4850-4853

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b02414

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Funding

  1. Ministry of Education, Culture, Sports, Science and Technology, Japan
  2. JST, ACT-C
  3. Asahi Glass Foundation

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We report here a method for direct catalytic introduction of simple alpha-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 a-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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