No abstract

We have developed a catalytic method for the hydroalkylation of allenes using alkyl triflates as electrophiles and silane as a hydride source. The reaction has an excellent substrate scope and is compatible with a wide range of functional groups, including esters, aryl halides, aryl boronic esters, sulfonamides, alkyl tosylates, and alkyl bromides. We found evidence for a reaction mechanism that involves unusual dinuclear copper ally complexes as catalytic intermediates. The unusual structure of these complexes provides a rationale for their unexpected reactivity.

We have developed ac atalytic method for the hydroalkylation of allenes using alkylt riflates as electrophiles and silane as ah ydride source.T he reaction has an excellent substrate scope and is compatible with aw ide range of functional groups,i ncluding esters,a ryl halides,a ryl boronic esters,s ulfonamides,a lkylt osylates,a nd alkylb romides.W e found evidence for areaction mechanism that involves unusual dinuclear copper ally complexes as catalytic intermediates.The unusual structure of these complexes provides ar ationale for their unexpected reactivity. Scheme 1. Copper-catalyzed hydroalkylation of allenes.