This paper describes the nickel-catalyzed reductive alkylation of aroyl fluorides with alkyl bromides in a decarbonylative manner. In this reaction, various functional groups are well tolerated and the C(sp 2 )−C(sp 3 ) bond can be constructed directly without the use of organometallic reagents. The present reaction is a cross-electrophile coupling via the radical pathway, affording the corresponding alkylarenes in moderate to good yields.

In this Letter, the palladium/copper-cocatalyzed arylsilylation of internal alkynes with acyl fluorides and silylboranes is described. This is the first example in which acyl fluorides have been utilized for the three-component coupling reaction via decarbonylation, yielding a variety of tetrasubstituted alkenylsilanes in moderate to good yields.

Copper-catalyzed carboazidation of alkenes with trimethylsilyl azide and cyclic ethers has been achieved. The employment of naturally abundant copper catalysts allowed cyclic ethers to be used as alkylating reagents under oxidative conditions. The use of styrene derivatives and 1,1-diaryl alkenes afforded carboazidation products. In addition, application of five-and six-membered cyclic ethers to the present reaction gave target organic molecules bearing azide and cyclic ether groups with perfect regioselectivity. Radical trapping and clock experiments revealed that the present reaction proceeded via the radical pathway. To further demonstrate the utility of this carboazidation reaction, transformations from the azide group to the related nitrogen-containing compounds were also performed.