4.8 Article

Transforming Benzylic Amines into Diarylmethanes: Cross-Couplings of Benzylic Pyridinium Salts via C-N Bond Activation

Journal

ORGANIC LETTERS
Volume 20, Issue 10, Pages 3030-3033

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b01062

Keywords

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Funding

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

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A nickel-catalyzed cross-coupling of benzylic pyridinium salts with arylboronic acids was developed. Coupled with chemoselective pyridinium formation, this method allows benzyl primary amines to be efficiently converted to di(hetero)-arylmethanes. Excellent heteroaryl and functional group tolerance is observed, and a one-pot procedure enables benzylic amines to be converted to diarylmethanes directly.

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