Palladium-Catalyzed Efficient and One-Pot Synthesis of Diarylacetylenes from the Reaction of Aryl Chlorides with 2-Methyl-3-butyn-2-ol

Authors

  • Chenyi Yi,

    1. Department of Chemistry, Tsinghua University, Innovative Catalysis Program, Key Laboratory of Organic Optoelectronics & Molecular Engineering of Ministry of Education, Beijing 100084, People's Republic of China, Fax: (+86)-10-6279-2596
    Search for more papers by this author
  • Ruimao Hua,

    1. Department of Chemistry, Tsinghua University, Innovative Catalysis Program, Key Laboratory of Organic Optoelectronics & Molecular Engineering of Ministry of Education, Beijing 100084, People's Republic of China, Fax: (+86)-10-6279-2596
    Search for more papers by this author
  • Hanxiang Zeng,

    1. Department of Chemistry, Tsinghua University, Innovative Catalysis Program, Key Laboratory of Organic Optoelectronics & Molecular Engineering of Ministry of Education, Beijing 100084, People's Republic of China, Fax: (+86)-10-6279-2596
    Search for more papers by this author
  • Qiufeng Huang

    1. Department of Chemistry, Tsinghua University, Innovative Catalysis Program, Key Laboratory of Organic Optoelectronics & Molecular Engineering of Ministry of Education, Beijing 100084, People's Republic of China, Fax: (+86)-10-6279-2596
    Search for more papers by this author

Abstract

An efficient and practical synthetic method has been developed for the preparation of symmetrical diarylacetylenes from the direct reaction of aryl chlorides with 2-methyl-3-butyn-2-ol catalyzed by palladium(II) chloride-bis(tricyclohexylphosphine) [PdCl2(PCy3)2] under mild reaction conditions. Unsymmetrical diarylated acetylenes could be also obtained by using two different aryl chlorides simultaneously. The catalytic procedure includes a novel one-pot palladium-catalyzed, double Sonogashira coupling of inactivated aryl chlorides without use of copper(I) as co-catalyst.

Ancillary