Highly Regio- and Stereoselective Three-Component Nickel-Catalyzed syn-Hydrocarboxylation of Alkynes with Diethyl Zinc and Carbon Dioxide

Authors

  • Suhua Li,

    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032 (P.R. China), Fax: (+86) 21-6260-9305
    Search for more papers by this author
  • Weiming Yuan,

    1. Shanghai Key Laboratory of Green Chemistry and Chemical Process, Department of Chemistry, East China Normal University, 3663 North Zhongshan Lu, Shanghai 200062 (P.R. China)
    Search for more papers by this author
  • Prof. Dr. Shengming Ma

    Corresponding author
    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032 (P.R. China), Fax: (+86) 21-6260-9305
    2. Shanghai Key Laboratory of Green Chemistry and Chemical Process, Department of Chemistry, East China Normal University, 3663 North Zhongshan Lu, Shanghai 200062 (P.R. China)
    • State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032 (P.R. China), Fax: (+86) 21-6260-9305
    Search for more papers by this author

  • Financial support from the Major State Basic Research and Development Program (2009CB825300), National Natural Science Foundation of China (20732005), and Project for Basic Research in Natural Science Issued by Shanghai Municipal Committee of Science (08dj1400100) is greatly appreciated. We thank Mr. Guobin Chai of our research group for reproducing the results presented in entry 2 of Table 2, entry 4 of Table 3, and Equation 1 in Scheme 3.

Abstract

original image

Hydrocarboxylation of alkynes: The first example of nickel-catalyzed hydrozincation of alkynes that form stereodefined hydrocarboxylation products is presented (see scheme; cod=cycloocta-1,5-diene). This catalytic system is efficient for the activation of CO2 and the three-component reaction produces products that could be converted into important oxindole or γ-butyrolactam derivatives.

Ancillary