4.8 Article

Enantioselective para-C(sp2)-H Functionalization of Alkyl Benzene Derivatives via Cooperative Catalysis of Gold/Chiral Bronsted Acid

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出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202208874

关键词

Arenes; C-H Bond Insertion; Cooperative Catalysis; Diazo Compounds; Site-Selective

资金

  1. National Natural Science Foundation of China [21971066, 22171088]
  2. Science and Technology Commission of Shanghai Municipality [18JC1412300]

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Asymmetric para-C(sp(2))-H bond functionalization of alkyl benzene derivatives was successfully achieved via cooperative catalysis of gold and chiral phosphoric acid (CPA). This method offers mild conditions, high efficiency, broad substrate scope, and extensive applications of the chiral products.
An asymmetric para-C(sp(2))-H bond functionalization of alkyl benzene derivatives was successfully developed via cooperative catalysis of gold and chiral phosphoric acid (CPA), leading to synthetically useful chiral 1,1-diaryl motifs. Chiral phosphoric acid, ligand, and molecular sieves were found to be crucial for enantioselectivity control of this transformation. The salient features of this protocol include mild conditions, high efficiency, commercially available starting materials, highly chemo- and site- as well as enantioselective aromatic C-H functionalization, broad substrate scope, and extensive applications of the chiral products. The mechanistic studies suggested that two CPAs might be involved in chiral induction.

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