4.4 Article

Substituted 1,3-cyclohexadiene synthesis by NHC-Nickel(0) catalyzed [2+2+2] cycloaddition of 1,n-Enyne

Journal

TETRAHEDRON
Volume 71, Issue 26-27, Pages 4426-4431

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2015.05.016

Keywords

N-Heterocyclic carbene (NHC); Nickel; Dimerization; Cycloaddition; 1,3-Dienes

Funding

  1. Thousand Young Talents Program Award
  2. SUSTC start up fund
  3. Guangdong Province Matching Fund [K12213101]

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This paper describes a catalytic and selective synthesis of substituted 1,3-cyclohexadiene fused with xH-pyran and furan. By using terminal enynes as substrates, NHC-Ni(0) as catalyst, and an ether as spacer between the two unsaturated hydrocarbon termini, the system competed with the terminal alkyne cyclotrimerization and yielded the desired [2+2+2] cycloaddition. (C) 2015 Elsevier Ltd. All rights reserved.

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