Consecutive cross-coupling reactions of 2,2-difluoro-1-iodoethenyl tosylate with boronic acids: efficient synthesis of 1,1-diaryl-2,2-difluoroethenes

• Ju Hee Kim,
• Su Jeong Choi and
• In Howa Jeong

Beilstein J. Org. Chem. 2013, 9, 2470–2475, doi:10.3762/bjoc.9.286

• Ju Hee Kim Su Jeong Choi In Howa Jeong Department of Chemistry & Medical Chemistry, Yonsei University, 1 Yonseidae-gil, Wonju, Gangwondo 220-710, Republic of Korea 10.3762/bjoc.9.286 Abstract The cross-coupling reactions of 2,2-difluoro-1-iodoethenyl tosylate (2) with 2 equiv of boronic acids in

• studied in the cross-coupling reaction with stable and less toxic nucleophilic metal reagents such as aryl- and alkenylboronic acids. Herein, we report a preparation of 2,2-difluoro-1-iodoethenyl tosylate and its cross-coupling reactions with aryl- and alkenylboronic acids to give the corresponding 1,1

• -difluoroalkenes. Results and Discussion Although the chemistry of the 2,2-difluoroethenylidene species as a building block has been well established in recent years, 2,2-difluoro-1-iodoethenyl tosylate (2) was not previously prepared. However, we easily synthesized the starting material 2 from the reaction of