137445-06-8Relevant articles and documents
Application of a 2-aryl indenylphosphine ligand in the Buchwald-Hartwig cross-coupling reactions of aryl and heteroaryl chlorides under the solvent-free and aqueous conditions
Liu, Yan,Yuan, Jia,Wang, Zi-Fei,Zeng, Si-Hao,Gao, Meng-Yue,Ruan, Mei-Lin,Chen, Jian,Yu, Guang-Ao
, p. 5805 - 5810 (2017)
An efficient solvent-free protocol for the Buchwald-Hartwig cross-coupling reaction of aryl and heteroaryl chlorides with primary and secondary amines using the Pd(dba)2/ligand 1 catalytic system has been developed. Notably, the catalytic system also efficiently catalyzed the reaction under aqueous conditions.
Synthetic approach for constructing the 1-oxygenated carbazole core and its application to the preparation of natural alkaloids
Bautista, Rafael,Jerezano, Alberto V.,Tamariz, Joaquin
, p. 3327 - 3336,10 (2012/12/11)
An efficient synthetic approach for the construction of the 1-oxygenated carbazole core is described. The condensation of cyclohexane-1,2-diones with a series of anilines yielded the corresponding 2-anilinocyclohex-2-en-1-ones, followed by the one-pot aromatization/methylation process of the latter to provide N-aryl-2-methoxyanilines. A palladium(II)-catalyzed cyclization of these N-aryl-2-methoxyanilines afforded the desired 1-methoxycarbazole frame in high overall yields. This protocol was implemented for the total synthesis of the naturally occurring glycozolicine and 6-methoxymurrayanine.
Synthetic approach for constructing the 1-oxygenated carbazole core and its application to the preparation of natural alkaloids
Bautista, Rafael,Jerezano, Alberto V.,Tamariz, Joaquín
, p. 3327 - 3336 (2013/01/15)
An efficient synthetic approach for the construction of the 1-oxygenated carbazole core is described. The condensation of cyclohexane-1,2-diones with a series of anilines yielded the corresponding 2-anilinocyclohex-2-en-1-ones, followed by the one-pot aromatization/methylation process of the latter to provide N-aryl-2-methoxyanilines. A palladium(II)-catalyzed cyclization of these N-aryl-2-methoxyanilines afforded the desired 1-methoxycarbazole frame in high overall yields. This protocol was implemented for the total synthesis of the naturally occurring glycozolicine and 6-methoxymurrayanine. Georg Thieme Verlag Stuttgart · New York.
Pyrrole-2-carboxylic acid as a ligand for the Cu-catalyzed reactions of primary anilines with aryl halides
Altman, Ryan A.,Anderson, Kevin W.,Buchwald, Stephen L.
, p. 5167 - 5169 (2008/12/20)
(Chemical Equation Presented) Pyrrole 2-carboxylic acid (L5) was found to be an effective ligand for the Cu-catalyzed monoarylation of anilines with aryl iodides and bromides. Under the reported conditions (10% CuI/20% L5/DMSO/K 3PO4
Unexpected multicomponent reaction of 2/4-methoxyarylaldehydes with arylhydroxylamines and maleic anhydride: a novel synthesis of unsymmetrical diarylamines
Sridharan,Karthikeyan,Muthusubramanian
, p. 4221 - 4223 (2007/10/03)
Unsymmetrical diarylamines have been synthesized by a novel, unexpected multicomponent reaction between methoxyarylaldehydes, N-arylhydroxylamine and maleic anhydride. A possible mechanism for the formation of the product is proposed. The reaction was also carried out under microwave irradiation.
Aryllead Triacetates: Regioselective Reagents for N-Arylation of Amines
Barton, Derek H. R.,Donnelly, Dervilla, M. X.,Finet, Jean-Pierre,Guiry, Patrick J.
, p. 2095 - 2102 (2007/10/02)
Aryllead triacetates have been found to be regioselective reagents for the mono N-arylation of a range of aromatic, heterocyclic and aliphatic amines under mild and neutral conditions in a reaction catalysed by copper diacetate.The arylation of arylamines was unaffected by the steric hindrance of the arylamine but was dependent on the arylamine basicity.In addition, the position of oxidisable substituents on both the aryllead triacetate and the arylamine was found to be important due to a competing oxidation-reduction reaction.The arylation of heterocyclic amines proceeded in modest to good yields whilst aliphatic amines were arylated in poor to modest yields.The mechanism proposed for these reactions involves transfer of the aryl group onto copper forming a copper(III) intermediate which subsequently undergoes ligand coupling to give the N-arylated amine and the catalytic CuI species.
