The Journal of organic chemistry

Intramolecular hydroboration of unsaturated phosphine boranes

P Shapland, E Vedejs

Index: Shapland, Peter; Vedejs, Edwin Journal of Organic Chemistry, 2004 , vol. 69, # 12 p. 4094 - 4100

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Citation Number: 12

Abstract

Homoallylic phosphine boranes undergo intramolecular hydroboration upon activation by triflic acid. The reaction occurs via an intermediate B-trifluorosulfonyloxyborane complex such as 15, followed by SN1-like or SN2-like displacement of the triflate leaving group, apparently leading to the formation of a four-center transition state. In the case of trisubstituted double bonds, as in the substrates 29 and 32, ionic hydrogenation of the ...

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