The development of a mild and general method for the alkylation of amides with relatively unreactive alkyl halides (i.e., poor substrates for SN2 reactions) is an ongoing challenge in organic synthesis. We describe herein a versatile transition-metal-catalyzed approach: in particular, a photoinduced, copper-catalyzed monoalkylation of primary amides. A broad array of alkyl and aryl amides (as w...

This paper deals with the synthesis of 2-deoxy-2-C-alkyl/aryl septanosides. A range of such septanoside derivatives was synthesized by using a common bromo-oxepine intermediate, involving C-C bond forming organometallic reactions. Unsaturated, seven-membered septanoside vinyl bromides or bromo-oxepines, obtained through a ring expansion methodology of the cyclopropane derivatives of oxyglycals,...

We report a novel example of electro-mediated photoredox catalysis (e-PRC) in the reductive cleavage C(sp3)?O bonds phosphinated alcohols to alkyl carbanions. As well as deoxygenations, olefinations are reported which E-selective and can be made Z-selective tandem reduction/photosensitization process where both steps photoelectrochemically promoted. Spectroscopy, computation, catalyst structura...

An efficient one-pot procedure combining bromide conversion into azide followed by NiAAC for the preparation of 1,5-disubstituted 1,2,3-triazoles has been developed. This prevents use isolated azides, which are insufficiently commercially available and could be potentially unstable difficult to handle. Moreover, this method tolerates a broad range functional moieties including ester, carbamate ...

Disclosed herein is the first general chemo- and site-selective alkylation of C-Br bonds in the presence of COTf, C-Cl and other potentially reactive functional groups, using the air-, moisture-, and thermally stable dinuclear PdI catalyst, [Pd(μ-I)PtBu3 ]2 . The bromo-selectivity is independent of the substrate and the relative positioning of the competing reaction sites, and as such fully pre...

Abstract Alkyl bromides are used as initiators in most of the atom transfer radical polymerization (ATRP) process and play an important role for controlling ATRP equilibrium. In this work, effect solvent on equilibrium constant ( K ) rate activation k act three isomeric alkyl [namely, N -phenyl(3-bromo-3-methyl)succinimide, -phenyl(3-bromo-4-methyl)succinimide, -phenyl(3-bromomethyl)succinimide...