Cation Radical-Accelerated Nucleophilic Aromatic Substitution for Amination of Alkoxyarenes

Venditto, Nicholas J.; Nicewicz, David A.

doi:10.1021/acs.orglett.0c01621

Cation Radical-Accelerated Nucleophilic Aromatic Substitution for Amination of Alkoxyarenes

Journal Article · Tue Jun 02 00:00:00 EDT 2020 · Organic Letters

DOI:https://doi.org/10.1021/acs.orglett.0c01621· OSTI ID:1801388

Venditto, Nicholas J. ^[1]; ^[2]

Univ. of North Carolina, Chapel Hill, NC (United States); OSTI
Univ. of North Carolina, Chapel Hill, NC (United States)

Nucleophilic aromatic substitution (S_NAr) is a common method for arene functionalization; however, reactions of this type are typically limited to electron-deficient aromatic halides. Herein, we describe a mild, metal-free, cation-radical accelerated nucleophilic aromatic substitution (CRA-S_NAr) using a potent, highly oxidizing acridinium photoredox catalyst. Selective substitution of arene C–O bonds on a wide array of aryl ether substrates was shown with a variety of primary amine nucleophiles. Mechanistic evidence is also presented that supports the proposed CRA-S_NAr pathway.

View Accepted Manuscript (DOE)

Research Organization:: Univ. of North Carolina, Chapel Hill, NC (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

Grant/Contract Number:: SC0001011

OSTI ID:: 1801388

Journal Information:: Organic Letters, Journal Name: Organic Letters Journal Issue: 12 Vol. 22; ISSN 1523-7060

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

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