4.7 Article

Palladium-Catalyzed, Copper(I)-Promoted Methoxycarbonylation of Arylboronic Acids with O-Methyl S-Aryl Thiocarbonates

期刊

JOURNAL OF ORGANIC CHEMISTRY
卷 85, 期 6, 页码 4475-4481

出版社

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c00198

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资金

  1. Shanghai Institute of Materia Medica
  2. Chinese Academy of Sciences
  3. NSFC [21772211]
  4. Youth Innovation Promotion Association CAS [2014229, 2018293]
  5. Science and Technology Commission of Shanghai Municipality [17JC1405000]
  6. Program of Shanghai Academic Research Leader [19XD1424600]
  7. National Science & Technology Major Project Key New Drug Creation and Manufacturing Program, China [2018ZX09711002-006]

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Here, we report O-methyl S-aryl thiocarbonates as a versatile esterification reagent for palladium-catalyzed methoxycarbonylation of arylboronic acid in the presence of copper(I) thiophene-2-carboxylate (CuTC). The reaction condition is mild, and a variety of substituents including sensitive -CI, -Br, and free -NH2 could be tolerated. Further applications in the late-stage esterification of some pharmaceutical drugs demonstrate the broad utility of this method.

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