The transformation of acid hydrazides to primary amides is of certain relevance for the organic synthesis of complex molecules. While existing methods require harsh reaction conditions, we present an electrochemical appr...
A new method is reported for preparing 1-chloroalkynes from alkynylsilanes using trichloroisocyanuric acid (TCCA) as chlorinating agent and AgNO3 for in situ desilylation. The method is selective for trimethylsilyl-prote...
We have developed convenient methods for the synthesis of symmetrical trisulfides under mild conditions in very good yields. The described methods are based oil the straightforward preparation of (5,5-dimethyl-2-thioxo-1...
1,2-Disubstituted cyclopropanes with different electron-withdrawing groups were accessed stereospecifically from similarly functionalized gamma-hydroxy-alpha,beta-unsaturated compounds.
Sonogashira coupling of methyl {4-[3-iodo-5-isopropyl-4-(methoxymethoxy)benzyl]-3,5-dimethylphenoxy}ac etate with (trimethylsilyl)acetylene afforded the corresponding (trimethylsilyl)ethynyl derivative in quantitative yi...
A highly practical method for the Synthesis Of fluorinated benzimidazoles was developed by Cul/TMEDA-catalyzed cross-coupling reaction of N-(2-haloaryl)trifluoroacetimidoyl chlorides with primary amines. The present doub...
A series of stereoisomeric ammonium salts containing the 1,2-dihydroxypropyl unit were prepared. Of particular interest to us are those salts that were found to be ionic liquids, although some are solids at room temperat...
Synthetic access to oxazolyl-substituted heterocycles including oxazolylimidazoles, -thiazoles, and -oxazoles is gained from a masked a-halo ketone attached to the 2-position of the oxazole ring. 3-Bromo-2,2-diethoxy-N-(...
A new synthetic protocol for the preparation of 3,3-disubstituted cyclopropenes from the corresponding bromocyclopropanes via a base-assisted 1,2-elimination has been developed. Employment of catalytic amounts of 18-crow...
Tosyl isocyanide and ethyl chloroformate react with nitrostyrenes to afford nitro-substituted pyrroles in good yield when a catch-and-re lease protocol was employed as a purification strategy.
2-(1-Alkoxyalkyl)-4-alkylidene-4H-3,1-benzoxazines are conveniently prepared by the reaction of 1-(2-ixocyanophenyl)ethanones or 1-(2-isocyanophenyl)propan-1-ones with a vinyl ether, such as 2-methyoxypropene or ethyl vi...
Functionalized heterohelicenes were prepared using sequential olefin metathesis and direct arylation reactions. Functionalization via C-H activation always occurs at the least hindered position of the [5]helicene carbon ...
The click reaction of azido- and ethynyl-functionalized terpyridines has been exploited to obtain a series of 1H-1,2,3-triazole-substituted terpyridines. This protocol was extended towards the synthesis of terpyridine-ba...
Ring opening of 2,2-dimethylthiirane by deactivated aromatic amines to afford 2-(arylamino)ethanethiols as 6-substituted 1,4-benzothiazine precursors, was investigated. The reaction takes place under mild conditions usin...
The direct sulfenylation of indoles with aromatic thiols has been accomplished in the presence of 20 mol% of FeCl3 in refluxing acetonitrile to produce 3-arylthioindoles in relatively good to excellent yields and with hi...
An unprecedented organocatalytic asymmetric Michael addition of fluorine-containing carbon-centered nucleophiles to nitroolefins has been described. The process features the creation of a fluorine-containing quaternary c...