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In this paper, we report an efficient approach for the direct fluoroalkylthiolation of indoles with iodofluoroethane in the presence of NaSO. In this work, we employed readily available iodofluoroethane and NaSO as fluoroalkylthiolation reagents, featuring mild conditions and a wide range of indole substrates. In addition, fluoroalkylthiolated 2,3'-biindole derivatives can also be prepared by this method.

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Remote functionalization reactions have the power to transform a C-H (or C-C) bond at a distant position from a functional group. This Review summarizes recent advances and key breakthroughs in remote fluorination, trifluoromethylation, difluoromethylation, trifluoromethylthiolation, and fluoroalkenylation reactions. Several powerful strategies have emerged to control the reactivity and distal selectivity such as the undirected radical approach, the 1,5-hydrogen atom transfer, the metal migration, the use of distant directing groups, and the ring-opening reactions.

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Fluoroalkylation of Diazo Compounds with Diverse R Reagents.

Chem Asian J

June 2020

School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, 205 Luoshi Road, Wuhan, 430070, China.

Progress in the transition-metal-catalyzed or -free fluoroalkylation of diazo compounds with different types of fluoroalkyl (R ) transfer reagents is summarized in this review. Special attention is focused on the straightforward trifluoromethylation, gem-difluoroolefination, trifluoromethoxylation, fluoroalkylthiolation, and trifluoromethylselenolation of diazo substrates. The mechanistic insights and the application of some of the products are also discussed in this article.

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Fluoroalkylsulfonyl Chlorides Promoted Vicinal Chloro-fluoroalkylthiolation of Alkenes and Alkynes.

Org Lett

April 2018

Centre for Green Chemistry and Department of Chemistry , University of Massachusetts Boston, 100 Morrissey Boulevard , Boston , Massachusetts 02125 , United States.

The unprecedented use of CFSOCl for direct bifunctional chloro-trifluoromethylthiolation of alkenes and alkynes is reported. CFSCl, which is generated by the reduction of PPh, undergoes electrophilic addition and then chlorination to give the bifunctionalized products without using an additional chlorine source. The method is also applicable for chloro-difluoromethylthiolation using CFHSOCl.

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