The activation of a section, or of all the carbons of thiophene by bromine in lithium-halogen exchange reactions, was implemented in a step-wise manner to facilitate the preparation of novel multiple Fischer carbene-bearing thiophene compounds.

The use of catalytic t-Bu-P4 base dramatically improved the performance of halogen-zinc exchange of aryl iodides, and the arylzinc derivatives were functionalized under copper-free reaction conditions.

For the first time it is shown that exceptionally electron-rich arene rings can be fluorinated exclusively during the reductive elimination reactions of diaryliodonium fluorides. The 5-methoxy[2.2]paracyclophan-4-yl directing group simultaneously reduces unproductive aryne chemistry and eliminates ligand exchange reactions by a combination of steric and electronic effects. Use of the cyclophane...

We prepared a novel fluorous deoxy-fluorination reagent N,N-diethyl--difluoro-[3,5-bis(1H,1H,2H,2H-perfluorodecyl)benzyl]amine (1b) from 3,5-diiodobenzoic acid (3b) via N,N-diethyl-3,5-bis(1H,1H,2H,2H-perfluorodecyl)benzamide (2b) in four steps and used it for the fluorination of alcohols and diols. After the fluorination reactions, the isolation of the products and recovery of 2b was perfor...

Selective functionalization reactions of aromatic and heteroaromatic halides with carbon, oxygen, and nitrogen nucleophiles have attracted much attention in the last decades. In addition to typical metal-catalyzed coupling reactions, direct functionalization of aryl halides through the formation of Grignard reagents offer new ways for the efficient construction of biologically interesting carbo...

To expand upon the recent pioneering reports of catalyzed sp(3) C-H fluorination methods, the next rational step is to focus on directing "radical-based fluorination" more effectively. One potential solution entails selective C-C bond activation as a prelude to selective fluorination. Herein, we report the tandem photocatalyzed ring-opening/fluorination reactions of cyclopropanols by 1,2,4,5-te...