Di- tert-butyl Peroxide-Mediated Radical C(sp2/sp3)-S Bond Cleavage and Group-Transfer Cyclization
A novel strategy of cascade radical C(sp2/sp3)-S bond cleavage and group-transfer cyclization is disclosed. Triggered by alkyl radicals, varieties of 2-isocyanoaryl thioethers containing aliphatic, aryl, and heteroaromatic groups can be cleaved and precisely reinstalled to give benzothiazole derivatives. Mechanistic studies reveal that the cascade reaction undertakes an intermolecular pathway, and the inner radical sources (R radicals) exhibit high priority over those of methyl radical origin from di-tert-butyl peroxide.
Luo, Kai,Yang, Wen-Chao,Wei, Kai,Liu, Yue,Wang, Jun-Ke,Wu, Lei
p. 7851 - 7856
(2019/10/11)
Mild and practical method for the α-arylation of nitriles with heteroaryl halides
A mild and transition-metal-free method for theα-arylation of a liphatic nitriles with activated heteroaryl halides was developed using NaHMDS o r KHMDS as base at ambient temperature. The key to the success of this method is generation of the nitrile anion in the presence of the heteroaryl halide. The method is applicable to both primary and secondary carbonitriles and a wide range of heteroaryl halides. Selective monoarylation was observed with primary carbonitriles. The operational simplicity and the mild reaction conditions add to the value of this methodas a practical alternative to the preparation of α-heteroaryl carbonitriles.
Klapars, Artis,Waldman, Jacob H.,Campos, Kevin R.,Jensen, Mark S.,McLaughlin, Mark,Chung, John Y. L.,Cvetovich, Raymond J.,Chen, Cheng-Yi
p. 10186 - 10189
(2007/10/03)
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