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

ABSTRACT: 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.

SUBMITTER: Liao J

PROVIDER: S-EPMC6005208 | biostudies-literature | 2018 May

REPOSITORIES: biostudies-literature

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

Liao Jennie J Guan Weiye W Boscoe Brian P BP Tucker Joseph W JW Tomlin John W JW Garnsey Michelle R MR Watson Mary P MP

Organic letters 20180510 10

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. ...[more]

PMID: 29745674

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