As anticipated, regioselectivity issues arose when sterically unhindered alkenes with long aliphatic chains were subjected to the conditions of Method A. For instance, ether 32 could be obtained in a good yield, albeit as a mixture of regioisomers (74%, rr 10:1). To address this challenge, we capitalized on existing knowledge of hydroboration methods, and introduced 9-BBN as the hydroboration agent (referred to as Method B, see also Section 7.3 in the Supplementary Information). Armed with this new set of conditions, we successfully achieved excellent regioselectivity in the synthesis of compound 32 (59%, rr >20:1). Similarly, a series of long-chain alkenes incorporating multiple functional groups proved amenable to these conditions, yielding the expected products as single regioisomers with excellent yields (33-34, 72-86%). The presence of an acetal functionality was also tolerated, leading to the formation of product 35 in a 30% yield. Moreover, the transformation worked well with vinylcyclohexene, affording compound 36 in an excellent yield of 90%. Intriguingly, when phenylcontaining alkenes were employed as substrates, the formation of alkylarenes 37 and 38 was observed (82-85%), while significant migration of the nickel center to the benzylic position was not detected. Once again, this underscores the potential of our methodology for functionalizing alkyl chain termini.