3165-71-7Relevant articles and documents
Reactions of 1-tosyl-3-substituted indoles with conjugated dienes under thermal and/or high-pressure conditions
Biolatto,Kneeteman,Paredes,Mancini
, p. 3906 - 3912 (2001)
The behavior of 1-tosyl-3-acetylindole (1a), N,N-diethyl-17tosyl-3-indoleglyoxylamide (1b), and 1-tosyl-3-nitroindole (1c) as dienophiles in Diels-Alder reactions under thermal and/or high-pressure conditions was explored with different dienes: isoprene (
Electrochemical Palladium-Catalyzed Intramolecular C—H Amination of 2-Amidobiaryls for Synthesis of Carbazoles
Gao, Xinlong,Lei, Aiwen,Wang, Pan,Wang, Qingqing,Zhang, Heng,Zhang, Xiaojing
, p. 143 - 148 (2020/12/18)
The synthesis of carbazoles based on the electrochemical Pd-catalyzed intramolecular C—H amination of 2-amidobiaryls through oxidative cross coupling has been achieved under mild reaction conditions. The reaction can be carried out in undivided cell without the addition of external chemical oxidant. Besides good functional group compatibility, the desired carbazoles can be scaled up and modified easily. Compared with previous methods, this protocol affords a simple and sustainable avenue for the construction of carbazoles.
Transition-Metal-Free and Visible-Light-Mediated Desulfonylation and Dehalogenation Reactions: Hantzsch Ester Anion as Electron and Hydrogen Atom Donor
Heredia, Micaela D.,Guerra, Walter D.,Barolo, Silvia M.,Fornasier, Santiago J.,Rossi, Roberto A.,Budén, Mariá E.
supporting information, p. 13481 - 13494 (2020/12/15)
Novel approaches for N- and O-desulfonylation under room temperature (rt) and transition-metal-free conditions have been developed. The first methodology involves the transformation of a variety of N-sulfonyl heterocycles and phenyl benzenesulfonates to the corresponding desulfonylated products in good to excellent yields using only KOtBu in dimethyl sulfoxide (DMSO) at rt. Alternately, a visible light method has been used for deprotection of N-methyl-N-arylsulfonamides with Hantzsch ester (HE) anion serving as the visible-light-absorbing reagent and electron and hydrogen atom donor to promote the desulfonylation reaction. The HE anion can be easily prepared in situ by reaction of the corresponding HE with KOtBu in DMSO at rt. Both protocols were further explored in terms of synthetic scope as well as mechanistic aspects to rationalize key features of desulfonylation processes. Furthermore, the HE anion induces reductive dehalogenation reaction of aryl halides under visible light irradiation.
