4.8 Article

Synthesis of Amide Enol 2-Iodobenzoates by the Regio- and Stereoselective Gold-Catalyzed Acyloxyalkynylation of Ynamides with Hypervalent Iodine Reagents

Journal

ORGANIC LETTERS
Volume 24, Issue 39, Pages 7101-7106

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c02161

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Funding

  1. CSC (China Scholarship Council)
  2. state of Baden-Wurttemberg (bwHPC)
  3. German Research Foundation (DFG)
  4. [INST 40/467-1 FUGG]

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Multisubstituted alkenes can be efficiently synthesized by a gold-catalyzed acyloxyalkynylation reaction, which proceeds under mild conditions and accepts a wide range of substrates, resulting in high yields.
Multisubstituted alkenes are accessible by a gold-catalyzed acyloxyalkynylation of ynamides with ethynylbenziodox-olones (EBXs) with perfect atom-economy. The EBX reagents transfer both the carboxylate as well as the alkynyl entity. Overall, this cascade comprises the in situ generation of an alkynyl gold(III) species, a stereoselective C(sp)-C(sp(2)) bond formation, and a C-O coupling at the alkynyl position of the ynamides. This reaction proceeds under mild conditions and accepts a wide range of substrates. A number of tetrasubstituted amide enol 2-iodobenzoates bearing different functional groups were obtained in good to excellent yields. DFT calculations explain the observed regioselectivity. The synthetic potential of the reaction was further demonstrated by a number of selected follow-up transformations.

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