Diversification of Amidyl Radical Intermediates Derived from C-H Aminopyridylation. Academic Article

abstract

• The N-activating substituents typically encountered in C-H amination chemistry are challenging to remove and have limited scope for synthetic elaboration. Here, we demonstrate that N-benzylaminopyridinium species provide a platform for synthetic elaboration via reductive N-N bond activation to unveil electrophilic N-centered radicals. These reactive intermediates can be trapped either via anti-Markovnikov olefin carboamination to provide access to tetrahydroisoquinolines or via aza-Rubottom chemistry with silyl enol ethers to provide -amino ketones.

authors

• Powers, David

published proceedings

• Org Lett

altmetric score

• 8.6

author list (cited authors)

• Maity, A., Roychowdhury, P., Herrera, R. G., & Powers, D. C.

citation count

• 6

complete list of authors

• Maity, Asim||Roychowdhury, Pritam||Herrera, Roberto G||Powers, David C

publication date

• April 2022

publisher

• American Chemical Society (ACS)  Publisher

published in

• Organic Letters  Journal

keywords

• Amination
• Catalysis
• Ethers
• Ketones
• Stereoisomerism

PubMed Central ID

• 35377670

Digital Object Identifier (DOI)

• 10.1021/acs.orglett.2c00869

start page

• 2762

end page

• 2766

volume

• 24

issue

• 14

URL

• http://dx.doi.org/10.1021/acs.orglett.2c00869