Catalytic Amide-Base System of TMAF and N(TMS) 3 for Deprotonative Coupling of Benzylic C(sp 3 )-H Bonds with Carbonyls

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10 Citations (Scopus)

Abstract

This paper describes that an amide-base generated in situ from tetramethylammonium fluoride (TMAF) and N(TMS) 3 catalyzes the deprotonative coupling of benzylic C(sp 3 )-H bonds with carbonyls to form stilbenes. A variety of methylheteroarenes (2-methylbenzothiophene, 2-methylbenzofuran, and 2-, 3-, or 4-methylpyridines) are used as nucleophiles. Application to enamine synthesis using DMF as an electrophile is also shown. The present system is effective for toluenes (4-phenyl-, 4-bromo-, 2-bromo-, and 4-chlorotoluenes) having low reactivity.

Original languageEnglish
Pages (from-to)2588-2592
Number of pages5
JournalOrganic letters
Volume21
Issue number8
DOIs
Publication statusPublished - 2019 Apr 19

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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