Asymmetric organocatalytic direct C(sp²)-H/C(sp³)-H oxidative cross-coupling by chiral iodine reagents.

Angew Chem Int Ed Engl

Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, 230026 (China).

Published: March 2014

AI Article Synopsis

  • Researchers developed a method for directly coupling C-H bonds in N(1),N(3)-diphenylmalonamides using chiral organoiodine catalysts.
  • The reaction selectively functionalizes four C-H bonds to produce diverse spirooxindoles with high enantioselectivity.
  • This study highlights the potential of chiral hypervalent organoiodine reagents as effective alternatives for catalyzing reactions involving less reactive C-H bonds.

Article Abstract

An asymmetric organocatalytic direct C-H/C-H oxidative coupling reaction of N(1),N(3)-diphenylmalonamides has been well established by using chiral organoiodine compounds as catalysts, wherein four C-H bonds were stereoselectively functionalized to give structurally diverse spirooxindoles with high levels of enantioselectivity. More importantly, the findings indicated that chiral hypervalent organoiodine reagents can serve as alternative catalysts for the creation of enantioselective functionalization of inactive C-H bonds.

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http://dx.doi.org/10.1002/anie.201309967DOI Listing

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