Vinylations with acyclic alkyl-DHPs gave more variable results, and VBO 4a proved to give higher yields than 2a. Primary and secondary alkyl groups were transferred in moderate yields (3i, 3j), and a series of homobenzylic substrates gave products 3k-3n in similar yields irrespective of substitution pattern. Better results were observed in transfer of secondary benzylic radicals, cf 3n with 3o. Heteroatom-substituted alkyl groups were well tolerated, giving ethers 3p and 3q in 71 and 66% yield, respectively. Interestingly, a free hydroxyl group resulted in superior yield compared to the unsubstituted alkyl chain (3r 82% vs 3j 39%). Substrates with the hydroxyl group protected as the corresponding silyl ether (3s), acetal (3t) or functionalized ester (3u) reacted smoothly, and alkenes bearing thioether and azido functionalities (3v, 3w) were well accommodated.