Open AccessPhotochemically-Mediated, Nickel-Catalyzed Synthesis of N-(Hetero)aryl Sulfamate Esters
Author(s) -
J. Miles Blackburn,
Anastasia Gant Kanegusuku,
Georgia Scott,
Jennifer L. Roizen
Publication year - 2019
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.9b02621
Subject(s) - chemistry , aryl , alkyl , catalysis , nucleophile , nickel , iridium , alkylation , palladium , transition metal , combinatorial chemistry , metal , organic chemistry
A general method is described for the coupling of (hetero)aryl bromides with O -alkyl sulfamate esters. The protocol relies on catalytic amounts of nickel and photoexcitable iridium complexes and proceeds under visible light irradiation at ambient temperature. This technology engages a broad range of simple and complex O -alkyl sulfamate ester substrates under mild conditions. Furthermore, it is possible to avoid undesirable N -alkylation, which was found to plague palladium-based protocols for N -arylation of O -alkyl sulfamate esters. These investigations represent the first use of sulfamate esters as nucleophiles in transition metal-catalyzed C-N coupling processes.