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An efficient regioselective hydrodifluoromethylation of unactivated alkenes with TMSCF₂CO₂Et at ambient temperature.
A mild, versatile and efficient method for the regioselective hydrodifluoromethylation of unactivated alkenes has been developed. This Ag-mediated Csp(3)-CF2 bond forming reaction provides easy… Expand
Silver-catalyzed oxidative decarboxylation of difluoroacetates: efficient access to C-CF2 bond formation.
A mild, versatile and efficient method for the silver(I)-catalyzed oxidative decarboxylative gem-difluoromethylenation has been developed. The radical cascade reaction comprises the addition of an… Expand
Accelerating unimolecular decarboxylation by preassociated acid catalysis in thiamin-derived intermediates: implicating Brønsted acids as carbanion traps in enzymes.
- R. Kluger, G. Ikeda, Qingyan Hu, P. Cao, J. Drewry
- Chemistry, Medicine
- Journal of the American Chemical Society
- 14 November 2006
Mandelylthiamin (MT) is formally the conjugate of thiamin and benzoylformate. It is the simplified analogue of the first covalent intermediate in benzoylformate decarboxylase. Although MT is the… Expand
Highly effective copper-mediated gem-difluoromethylenation of arylboronic acids.
A copper-mediated gem-difluoromethylenation of aryl, heteroaryl and vinyl boronic acids with bromodifluoromethylated oxazole or thiazole derivatives has been developed. This novel reaction showed an… Expand
Novel and highly efficient DNA photocleavers: hydroperoxides of heterocyclic-fused naphthalimides
Abstract A series of novel hydroperoxides of heterocyclic-fused naphthalimides were designed, synthesized and exhibited excellent DNA photonicking activities. Among these compounds, the… Expand
Reactivity of intermediates in benzoylformate decarboxylase: avoiding the path to destruction.
Benzoylformate decarboxylase forms a covalent intermediate from thiamin diphosphate (TDP) and benzoylformate, alpha-mandelylTDP. This loses carbon dioxide to form a carbanion (enamine). Protonation… Expand
Making thiamin work faster: acid-promoted separation of carbon dioxide.
The conjugate of thiamin and benzoylformate, mandelylthiamin (MTh), undergoes decarboxylation about 106 times slower than the analogous enzymic intermediate. It has now been discovered that the… Expand
Enantioselective Fluorination of 2‐Oxindoles by Structure‐Micro‐Tuned N‐Fluorobenzenesulfonamides
We describe our attempts to fine-tune the reactivity and selectivity of N-fluorobenzenesulfonamide in fluorination reactions by changing the substituents on its phenyl rings. A series of… Expand
Fragmentation of the conjugate base of 2-(1-hydroxybenzyl)thiamin: does benzoylformate decarboxylase prevent orbital overlap to avoid it?
The base-catalyzed addition of thiamin to benzaldehyde produces 2-(1-hydroxybenzyl)thiamin (HBnT), but in neutral solution HBnT undergoes base-catalyzed irreversible fragmentation into pyrimidine and… Expand
Silver-Mediated C–H Difluoromethylation of Arenes
The first AgI-mediated C–H ethoxycarbonyl difluoromethylation with TMSCF2COOEt (TMS = trimethylsilyl) has been developed. The radical difluoromethylation proceeds smoothly to give the… Expand