19120-39-9Relevant articles and documents
Radical induced disproportionation of alcohols assisted by iodide under acidic conditions
Huang, Yang,Jiang, Haiwei,Li, Teng,Peng, Yang,Rong, Nianxin,Shi, Hexian,Yang, Weiran
, p. 8108 - 8115 (2021/10/29)
The disproportionation of alcohols without an additional reductant and oxidant to simultaneously form alkanes and aldehydes/ketones represents an atom-economical transformation. However, only limited methodologies have been reported, and they suffer from a narrow substrate scope or harsh reaction conditions. Herein, we report that alcohol disproportionation can proceed with high efficiency catalyzed by iodide under acidic conditions. This method exhibits high functional group tolerance including aryl alcohol derivatives with both electron-withdrawing and electron-donating groups, furan ring alcohol derivatives, allyl alcohol derivatives, and dihydric alcohols. Under the optimized reaction conditions, a 49% yield of 5-methyl furfural and a 49% yield of 2,5-diformylfuran were obtained simultaneously from 5-hydroxymethylfurfural. An initial mechanistic study suggested that the hydrogen transfer during this redox disproportionation occurred through the inter-transformation of HI and I2. Radical intermediates were involved during this reaction.
Potassium-Zincate-Catalyzed Benzylic C?H Bond Addition of Diarylmethanes to Styrenes
Liu, Yu-Feng,Zhai, Dan-Dan,Zhang, Xiang-Yu,Guan, Bing-Tao
supporting information, p. 8245 - 8249 (2018/02/26)
Direct functionalization of the benzylic C?H bond of diarylmethanes is an important strategy for the synthesis of diarylmethine-containing compounds. However, the methods developed to date for this purpose require a stoichiometric amount (usually more) of either a strong base or an oxidant. Reported here is the first catalytic benzylic C?H bond addition of diarylmethanes to styrenes and conjugated dienes. A potassium zincate complex, generated from potassium benzyl and zinc amide, acts as a catalyst and displays good activity and chemoselectivity. Considering the atom economy of the reaction and the ready availability of the catalyst, this reaction constitutes a practical, efficient method for diarylalkane synthesis.
Formal carbon insertion of n-tosylhydrazone into B-B and B-Si bonds: Gem-diborylation and gem-silylborylation of sp3 carbon
Li, Huan,Shangguan, Xianghang,Zhang, Zhikun,Huang, Shan,Zhang, Yan,Wang, Jianbo
supporting information, p. 448 - 451 (2014/04/03)
A convenient method is developed to synthesize 1,1-diboronates from the corresponding N-tosylhydrazones. This method is also applicable to synthesize 1-silyl-1-boron compounds. Meanwhile, derivatization and consecutive Pd-catalyzed cross-coupling reaction