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Palladium-Catalyzed Synthesis of α-Trifluoromethyl Benzylic Amines via Fluoroarylation of gem-Difluoro-2-azadienes Enabled by Phosphine-Catalyzed Formation of an Azaallyl-Silver Intermediate.

Publication ,  Journal Article
Daniel, PE; Onyeagusi, CI; Ribeiro, AA; Li, K; Malcolmson, SJ
Published in: ACS catalysis
January 2019

We report the synthesis of α-trifluoromethyl benzylic amines through the vicinal fluoroarylation of gem-difluoro-2-azadienes. Our studies indicate that XPhos plays an important role as a phase transfer catalyst that promotes the addition of AgF to the difluoroazadiene, generating an α-trifluoromethyl azaallyl-silver intermediate that we have characterized by NMR spectroscopy. This intermediate likely transmetallates to Pd, coupling several aryl iodides to deliver products in up to 90% yield. Modification of the azadiene's activating group facilitates challenging cross-couplings.

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Published In

ACS catalysis

DOI

EISSN

2155-5435

ISSN

2155-5435

Publication Date

January 2019

Volume

9

Issue

1

Start / End Page

205 / 210

Related Subject Headings

  • 3406 Physical chemistry
  • 3405 Organic chemistry
  • 3106 Industrial biotechnology
  • 0904 Chemical Engineering
  • 0305 Organic Chemistry
  • 0302 Inorganic Chemistry
 

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Daniel, P. E., Onyeagusi, C. I., Ribeiro, A. A., Li, K., & Malcolmson, S. J. (2019). Palladium-Catalyzed Synthesis of α-Trifluoromethyl Benzylic Amines via Fluoroarylation of gem-Difluoro-2-azadienes Enabled by Phosphine-Catalyzed Formation of an Azaallyl-Silver Intermediate. ACS Catalysis, 9(1), 205–210. https://doi.org/10.1021/acscatal.8b03999
Daniel, Paige E., Chibueze I. Onyeagusi, Anthony A. Ribeiro, Kangnan Li, and Steven J. Malcolmson. “Palladium-Catalyzed Synthesis of α-Trifluoromethyl Benzylic Amines via Fluoroarylation of gem-Difluoro-2-azadienes Enabled by Phosphine-Catalyzed Formation of an Azaallyl-Silver Intermediate.ACS Catalysis 9, no. 1 (January 2019): 205–10. https://doi.org/10.1021/acscatal.8b03999.
Journal cover image

Published In

ACS catalysis

DOI

EISSN

2155-5435

ISSN

2155-5435

Publication Date

January 2019

Volume

9

Issue

1

Start / End Page

205 / 210

Related Subject Headings

  • 3406 Physical chemistry
  • 3405 Organic chemistry
  • 3106 Industrial biotechnology
  • 0904 Chemical Engineering
  • 0305 Organic Chemistry
  • 0302 Inorganic Chemistry