4.8 Article

Site-Tunable Csp3- H Bonds Functionalization by Visible-Light-Induced Radical Translocation of N-Alkoxyphthalimides

Journal

ORGANIC LETTERS
Volume 21, Issue 22, Pages 9147-9152

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b03524

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Funding

  1. National Natural Science Foundation of China [21801220, 21472218, 21672183]
  2. Natural Science Foundation of Jiangsu Province [BK20180892]
  3. Priority Academic Program Development of Jiangsu Higher Education Institutions
  4. Top-notch Academic Programs Project of Jiangsu Higher Education Institutions

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Site-tunable functionalization of C(sp(3))-H bonds has been accomplished through radical translocation and cross-coupling. Upon irradiation with visible light, copper-based. photocatalyst [Cu(Xantphos)(dmp)]BF4 enabled cross-coupling of N-alkoxyphthalimides with amino acid esters or amino acids to provide delta-C(sp(3))-H alkylated alcohols (31 examples, up to 92% yield) with additive BNDHP or alpha-C(sp(3))-H alkylated alcohols (18 examples, up to 86% yield) with additive DABCO in a highly regioselective fashion.

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