2017
DOI: 10.1016/j.tet.2017.05.018
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Synthesis of benzimidazoles from o -phenylenediamines and DMF derivatives in the presence of PhSiH 3

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Cited by 39 publications
(23 citation statements)
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“…Later, the group of Sakai described a general and effective method catalyzed by indium tribromide, where more than 25 alkyl amines were obtained in high yields by using different amides as the N‐alkylating sources (Scheme B) . In the same year, the groups of Liu and Sun reported an elegant catalyst‐free method for the synthesis of benzimidazoles by the N‐methylation of o ‐phenylenediamines with DMF derivatives and PhSiH 3 . More than 15 different compounds were obtained in good to excellent yields.…”
Section: Catalytic Reductive N‐alkylation Of Amines Using Hydrosilanes As Reductantmentioning
confidence: 99%
“…Later, the group of Sakai described a general and effective method catalyzed by indium tribromide, where more than 25 alkyl amines were obtained in high yields by using different amides as the N‐alkylating sources (Scheme B) . In the same year, the groups of Liu and Sun reported an elegant catalyst‐free method for the synthesis of benzimidazoles by the N‐methylation of o ‐phenylenediamines with DMF derivatives and PhSiH 3 . More than 15 different compounds were obtained in good to excellent yields.…”
Section: Catalytic Reductive N‐alkylation Of Amines Using Hydrosilanes As Reductantmentioning
confidence: 99%
“…To show the merit of title methodology for the synthesis of 2aryl-1H-benzimidazole derivatives, the reaction conditions and the catalytic performance of a number of catalysts in literature, are summarized in Table 4 in comparison with this work. [35][36][37][38][39][40][41][42][43][44][45][46] Most of the catalysts given in Table 4, suffer seriously from toxicity and high catalyst dose. Additionally, they require toxic solvents and tedious work-up procedures or long reaction times.…”
Section: Comparison With Other Catalytic Systemsmentioning
confidence: 99%
“…New metal-catalyzed and metal-free conditions involving the CH of the formyl group of DMF have been reported for cyclizations leading to heterocycles (Equations (69) [ 80 , 81 , 82 ] and (70) [ 83 ]).…”
Section: R C Fragmentmentioning
confidence: 99%
“…2-Methylbenzimidazoles were obtained from PhSiH 3 -assisted delivery of the CMe of DMAc to benzene-1,2-diamines (Equation (71)) [ 82 ].…”
Section: R C Fragmentmentioning
confidence: 99%