Exploration of the Fluoride Reactivity of Aryltrifluoroborate on Selective Cleavage of Diphenylmethylsilyl Groups. Issue 29 (2nd July 2020)

• Record Type: Journal Article
• Authors: Fujiki, Katsumasa; Tanaka, Katsunori
• Is Part Of: European journal of organic chemistry. Issue 29(2020)
• Page Start: 4616
• Page End: 4620
• Publication Date: 2020-07-02
• Subjects: Trifluoroborates -- Fluorides -- Desilylation -- Reaction mechanisms -- Organocatalysis; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202000707
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : The first known report on the fluoride catalytic reactivity of potassium aryltrifluoroborate is described. The fluoride reactivity of phenyltrifluoroborate was controlled by substituents on the trifluoroborate‐attached benzene, such as the methoxy group at the para ‐position and the methyl group at the ortho ‐position. In addition, the selective aryltrifluoroborate‐catalyzed cleavage of the diphenylmethylsilyl group was achieved. Abstract : The unique fluoride reactivity of phenyltrifluoroborate in the desilylation of diphenylmethylsilyl groups is controlled by substituents on the benzene ring. The fluorine on trifluoroborate interacts with silicon and activates the Si–O bond to enable selective desilylation of the diphenylmethylsilyl group. Selective desilylation of a primary silyl ether in the presence of a secondary silyl ether by the trifluoroborate was also successful.