The dihalogenation of alkenes is the most direct and effective method for the synthesis of vicinal dihalides. Because there is always an exchange process between the chiral haloniums and the unreacted olefins to cause racemization, the development of catalytic enantioselective dihalogenation of alkenes ...
The α-halogenation of α,β-unsaturated carbonyls and dihalogenation of alkenes using bisacetoxyiodobenzene/pyride hydrohalides. Marsewi Ngatimin, Christopher J. Gartshore, Jeremy Kindler, Sudha Naidu, David W. Lupton* Tetrahedron Lett. 2009, 50, 6008 Citations: 5...
However, robust catalytic methods to perform dihalogenation in a stereoselective manner are lacking, despite the ubiquity of contiguous halogen-bearing stereocentres in natural products, bioactive and pharmaceutical molecules. Here we show that a urea directing moiety judiciously installed on alkenes could...
alkenesalpha-trifluoromethyl carbaniondihalogenationfluorinationpotassium fluorideA novel strategy for 1,2-dihalogenation of alkenes is reported that occurs via sequential nucleophilic halide addition and electrophilic halogenation. By trapping the in situ generated unstable α-trifluoromethyl carbanion intermediates...
Fig. 1: Deconstructive functionalization of alkenes. aCommon strategies for C=C bond cleavage.bVisible-light-mediated deconstructive oxidative geminal dihalogenation of trisubstituted alkenes (this work). DIH 1,3-diiodo-5,5-dimethyl-hydantoin, NBSN-bromosuccinimide, mCPBAmeta-chloroperoxybenzoic acid....
The combination of benzamide and NCS was found to be an efficient nitrogen/halogen source for aminohalogenation of β-nitrostyrenes. The reaction was c
Although recent years have witnessed significant advances in the development of catalytic, enantioselective halofunctionalizations of alkenes, the related dihalogenation of olefins to afford enantioenriched vicinal dihalide products remains comparatively underdeveloped. However, the growing number of complex ...
However, robust catalytic methods to perform dihalogenation in a stereoselective manner are lacking, despite the ubiquity of contiguous halogen-bearing stereocentres in natural products, bioactive and pharmaceutical molecules. Here we show that a urea directing moiety judiciously installed on alkenes could...
A procedure for the α-chlorination or bromination of a number of α,β-unsaturated carbonyls, and the dichlorination or bromination of alkenes, is developed using bisacetoxyiodobenzene (BAIB) and the HCl or HBr salt of pyridine. The reaction proceeds in an acceptable to a good yield and has...
We established a straightforward electrochemical dihalogenation (F, Cl, and Br) process for gem-difluoroalkenes. This reaction exhibits a broad functional group tolerance and has been effectively utilized in the construction of complex molecules. The subsequent synthetic transformations...