3552-02-1Relevant articles and documents
Convenient preparation of cycloalkenyl boronic acid pinacol esters
Rauniyar, Vivek,Zhai, Huimin,Hall, Dennis G.
, p. 3984 - 3995 (2008)
A practical method for the preparation of cycloalkenyl boronic acid pinacol esters is described. These important synthetic intermediates are typically made using more expensive methods like transition metal-catalyzed borylation of alkenyl halides or trifl
Umpolung Difunctionalization of Carbonyls via Visible-Light Photoredox Catalytic Radical-Carbanion Relay
Wang, Shun,Cheng, Bei-Yi,Sr?en, Matea,K?nig, Burkhard
supporting information, p. 7524 - 7531 (2020/08/05)
The combination of photoredox catalysis with the Wolff-Kishner (WK) reaction allows the difunctionalization of carbonyl groups by a radical-carbanion relay sequence (photo-Wolff-Kishner reaction). Photoredox initiated radical addition to N-sulfonylhydrazones yields α-functionalized carbanions following the WK-type mechanism. With sulfur-centered radicals, the carbanions are further functionalized by reaction with electrophiles including CO2 and aldehydes, whereas CF3 radical addition furnishes a wide range of gem-difluoroalkenes through β-fluoride elimination of the generated α-CF3 carbanions. More than 80 substrate examples demonstrate the broad applicability of this reaction sequence. A series of investigations including radical inhibition, deuterium labeling, fluorescence quenching, cyclic voltammetry, and control experiments support the proposed radical-carbanion relay mechanism.
Catalytic enantioselective allylboration of propargylic aldehydes
Bhakta, Urmibhusan,Sullivan, Erin,Hall, Dennis G.
supporting information, p. 678 - 683 (2014/02/14)
Homoallylic propargylic alcohols are important building blocks in natural product synthesis. This moiety can be transformed into various other structures by performing other known transformations, which can in turn lead to the synthesis of biologically us