4489-84-3Relevant articles and documents
Straightforward conversion of alcohols into dibenzenesulfonimides
Giovanelli, Emerson,Doris, Eric,Rousseau, Bernard
, p. 8457 - 8458 (2006)
The reaction of various alcohols with N-fluorodibenzenesulfonimide and triphenylphosphine leads to the corresponding dibenzenesulfonylated amines in high yields.
A Relay Strategy Actuates Pre-Existing Trisubstituted Olefins in Monoterpenoids for Cross-Metathesis with Trisubstituted Alkenes
Bahou, Karim A.,Braddock, D. Christopher,Meyer, Adam G.,Savage, G. Paul,Shi, Zhensheng,He, Tianyou
, p. 4906 - 4917 (2020/04/10)
A retrosynthetic disconnection-reconnection analysis of epoxypolyenes - substrates that can undergo cyclization to podocarpane-type tricycles - reveals relay-actuated Δ6,7-functionalized monoterpenoid alcohols for ruthenium benzylidene catalyzed olefin cross-metathesis with homoprenyl benzenes. Successful implementation of this approach provided several epoxypolyenes as expected (E/Z, ca. 2-3:1). The method is further generalized for the cross-metathesis of pre-existing trisubstituted olefins in other relay-actuated Δ6,7-functionalized monoterpenoid alcohols with various other trisubstituted alkenes to form new trisubstituted olefins. Epoxypolyene cyclization of an enantiomerically pure, but geometrically impure, epoxypolyene substrate provides an enantiomerically pure, trans-fused, podocarpane-type tricycle (from the E-geometrical isomer).
Dehydroxylative Fluorination of Tertiary Alcohols
Zhang, Wei,Gu, Yu-Cheng,Lin, Jin-Hong,Xiao, Ji-Chang
supporting information, p. 6642 - 6646 (2020/09/02)
A large number of fluorination methods have been developed, but the construction of a tertiary C-F bond remains challenging. Herein, we describe an efficient dehydroxylative fluorination of tertiary alcohols with Selectfluor via the activation of a hydroxyl group by a Ph2PCH2CH2PPh2/ICH2CH2I system. Although the reagents appear to be not compatible (Selectfluor with the phosphine and I- generated in situ), the reactions occur rapidly to give the desired products in moderate to high yields. This work may present a new discovery in fluorination of alcohols since the reported methods are mainly limited to primary and secondary alcohols.