4.5 Article

Vinylation of Benzylic Amines via C-N Bond Functionalization of Benzylic Pyridinium Salts

Journal

SYNTHESIS-STUTTGART
Volume 50, Issue 16, Pages 3231-3237

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0037-1610084

Keywords

allyl complexes; amines; benzylation; catalysis; cross-coupling; nickel

Funding

  1. NIH [R01 GM111820, NIH P20 GM104316, P20 GM103541, S10 OD016267]
  2. UD
  3. NSF [NSF CHE0421224, CHE1229234, CHE0840401, CHE1048367]
  4. NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM111820, P20GM103541, P30GM110758, P20GM104316] Funding Source: NIH RePORTER
  5. OFFICE OF THE DIRECTOR, NATIONAL INSTITUTES OF HEALTH [S10OD016267] Funding Source: NIH RePORTER

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Cross-couplings of benzylic pyridinium salts and vinylboronic acids or esters have been developed. Via benzylic pyridinium intermediates, benzylic amines can be engaged in these cross-couplings through C-N bond functionalization. This method boasts mild reaction conditions and excellent tolerance for heteroaryl substituents and a range of functional groups.

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