- Iridium-catalyzed intramolecular C–N and C–O/S cross-coupling reactions: Preparation of benzoazole derivatives
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The irdium-catalyzed intramolecular arylcarbon-hetero cross-coupling reactions with o-haloarylamides or o-haloarylamidine have been effectively achieved using KOAc and just 1 mol% catalyst. The [Ir(cod)Cl]2 was proved to be more potential for smoothly assembling functional structures benzimidazoles, benzoxazoles and benzothiazoles, which was superior to Cu- and Pd-catalyzed systems. Simultaneously, a concise and efficient synthesis of tafamidis was developed in 5-g scale.
- Shi, Yajie,Zhou, Qifan,Du, Fangyu,Fu, Yang,Du, Yang,Fang, Ting,Chen, Guoliang
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- Transition-metal-free synthesis of benzimidazoles mediated by KOH/DMSO
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Benzimidazoles are prepared by intramolecular N-arylations of amidines mediated by potassium hydroxide in DMSO at 120 °C. In this manner, diversely substituted products have been obtained in moderate to very good yields.
- Baars, Hannah,Beyer, Astrid,Kohlhepp, Stefanie V.,Bolm, Carsten
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supporting information
p. 536 - 539
(2014/04/03)
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- Reactivity-controlled regioselectivity: A regiospecific synthesis of 1,2-disubstituted benzimidazoles
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We demonstrate exceptional levels of regioselectivity in the tandem, animation reactions between 1,2-differentiated dihaloarenes and N-substituted amidines, The regiochemical outcome of this Cul-catalyzed reaction is achieved through a combination of N1/N2 chemoselectivity on the amidine and reactivity-controlled X1/X2 chemoselectivity on the 1,2-dihaloarene. This reaction proves to be fairly general for the regiospecific synthesis of 1,2-substituted benzimidazoles.
- Deng, Xiaohu,Mani, Neelakandha S.
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experimental part
p. 680 - 686
(2010/03/04)
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- A palladium-catalyzed regiospecific synthesis of N-aryl benzimidazoles
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(Chemical Equation Presented) Highly tolerated: A catalytic method employing [Pd2(dba)3] and XPhos or RuPhos permits the efficient synthesis of N-aryl benzimidazoles in regioisomerically pure form starting from ortho-halo-anilides (see scheme), and tolerates a wide range of functional groups, dba = trans,trans-dibenzylideneacetone.
- Zheng, Nan,Anderson, Kevin W.,Huang, Xiaohua,Nguyen, Hanh Nho,Buchwald, Stephen L.
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p. 7509 - 7512
(2008/09/17)
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