4286-86-6Relevant academic research and scientific papers
Alkene homologation: via visible light promoted hydrophosphination using triphenylphosphonium triflate
Levin, Vitalij V.,Dilman, Alexander D.
supporting information, p. 749 - 752 (2021/02/03)
A hydrophosphination reaction of alkenes with triphenylphosphonium triflate under photocatalytic conditions is described. The reaction is promoted by naphthalene-fused N-acylbenzimidazole and is believed to proceed through intermediate formation of a phosphinyl radical cation. The resulting phosphonium salts are directly involved in the Wittig reaction leading to homologated alkenes.
Migratory Arylboration of Unactivated Alkenes Enabled by Nickel Catalysis
Wang, Wang,Ding, Chao,Li, Yangyang,Li, Zheqi,Li, Yuqiang,Peng, Long,Yin, Guoyin
, p. 4612 - 4616 (2019/03/13)
An unprecedented arylboration of unactivated terminal alkenes, featuring 1,n-regioselectivity, has been achieved by nickel catalysis. The nitrogen-based ligand plays an essential role in the success of this three-component reaction. This transformation displays good regioselectivity and excellent functional-group tolerance. In addition, the incorporation of a boron group into the products provides substantial opportunities for further transformations. Also demonstrated is that the products can be readily transformed into pharmaceutically relevant molecules. Unexpectedly, preliminary mechanistic studies indicate that although the metal migration favors the α-position of boron, selective and decisive bond formation is favored at the benzylic position.
Photocatalytic Barbier reaction-visible-light induced allylation and benzylation of aldehydes and ketones
Berger, Anna Lucia,Donabauer, Karsten,K?nig, Burkhard
, p. 7230 - 7235 (2018/10/02)
We report a photocatalytic version of the Barbier type reaction using readily available allyl or benzyl bromides and aromatic aldehydes or ketones as starting materials to generate allylic or benzylic alcohols. The reaction proceeds at room temperature under visible light irradiation with the organic dye 3,7-di(4-biphenyl)1-naphthalene-10-phenoxazine as a photocatalyst and DIPEA as sacrificial electron donor. The proposed cross-coupling mechanism of a ketyl- and an allyl or benzyl radical is supported by spectroscopic investigations and cyclic voltammetry measurements.
