An
intermolecular electrochemical coupling between the benzylic
C(sp3)–H bond and various secondary amines is reported.
The electronic behavior of two electronically rich units viz the α-position
of α-aryl acetates and amines was engineered electrochemically,
thus facilitating their reactivity for the direct access of α-amino
esters. A series of acyclic/cyclic secondary amines and α-aryl
acetates were tested to furnish the corresponding α-amino esters
with high yields (up to 92%) under mild conditions.
An electrochemical method has been developed to synthesize
2,2-disubstituted
indolin-3-ones under mild conditions. A series of nucleophiles have
been added to the 2-arylindole-3-ones, generated in situ under metal-free
electrochemical oxidative dearomatization of 2-arylindoles, to afford
2,2-disubstituted 3-carbonyl indoles with heteroquaternary centers
in 57–79% yields.
A straightforward method has been developed to synthesize
2-aryl-3-(2-aminoaryl)
quinoxalines from 2-arylindoles and 1,2-diaminoarenes under mild electrochemical
conditions. The reaction proceeds through in situ generations of 2-arylindole-3-ones
under electrochemical oxidative dearomatization of 2-arylindoles,
followed by a ring opening-cyclization sequence with 1,2-diaminoarenes.
A series of 2-aryl-3-(2-aminoaryl) quinoxalines have been prepared
with moderate to good yields (up to 75%).
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.