Nickel-catalyzed Hydroboration Andhydrosilylation Of Alkenes In An Alcoholic Solvent

Olefins are bulky raw materials in chemical industry,and the development of their transformation reactions has been always a main topic in organic chemistry.Transition metal-catalyzed olefin functionalization provides a versatile way for transformations of olefins into other high value-added chemicals.A series of functionalized methods to form various chemical bonds,such as C-C,C=C,C-Ar,C-O,C-N and C-X bond have been developed during past decades.Organoboron and organosilicon compounds are two important compounds that have been widely used in formations of new C-C bonds,C-N bonds and C-O bonds in organic synthesis,medicine and materials.Therefore,it is of great significance to develop novel and efficient methods for building C-B and C-Si bonds.In this paper,we have developed a Ni-catalyzed hydroboration and hydrosilylation reaction of olefins using alcohol as the hydride source and solvent,providing a series of alkyl organoboron and organosilicon compounds.1.A Ni-catalyzed linear-selective hydroboration of simple olefin and B2pin2 was developed,in which methanol as solvent and hydride source proved to be critical,avoiding the use of additional base.A series of organoboron compounds can be obtained in 49-93% yield from either less-activated styrene and its derivatives or unactivated alkyl olefins.2.A Ni-catalyzed linear-selective hydrosilylation of styrene and its derivatives and Me2 Ph Si Bpin was developed,in which methanol was still used as solvent and hydride source.A series of organosilicon compounds can be obtained in 51-95%yield.