Journal of the Chemical Society. Perkin transactions I p. 2083 - 2096 (1995)
Update date:2022-08-03
Topics:
Trost, Barry M.
Spagnol, Michel D.
Allylamines function as substrates for cross-coupling with boronic acids in the presence of nickel(0) catalysts rather than palladium(0) catalysts.Aryl-, vinyl- and methyl-boronic acids function well.With vinyl derivatives, E-isomers couple more efficiently than Z-isomer and both fully retain the geometrical integrity.Methylations preferably employ the boronic esters like 2-methyl-1,3,2-benzodioxaborole or 2-methyl-1,3,2-dioxaborolane rather than methylboronic acid.The stereochemistry of the reaction involves a net inversion with respect to the allylamine.The regioselectivity is a function of ligand.Generally, sterically bulky donor phosphines promote new C-C bond formation at the less substituted position.Bidentate ligands, notably 1,1'-binaphthyl-2,2'-ylbis(diphenylphosphinite) (BINAPO), promote new C-C bond formation at the more substituted allyl terminus.The amines appear to be the preferred partner compared to allyl alcohols and esters with the boronic acids and give higher stereospecificity.
View MoreXinjiang Zhongtai Chemical Co., Ltd.
Contact:+86-991-8788172
Address:NO.78 XISHAN RD.URUMQI，CHINA
hangzhou verychem science and technology co.ltd
website:http://www.verypharm.com
Contact:+86-571-88162785; 88162786
Address:F1502, 753 Shenhua road, Hangzhou, China
CGeneTech (Suzhou, China) Co., Ltd.
Contact:+86-512-62956962
Address:Room 101，Bld C11,218 Xinghu Rd.,Suzhou industrial Park
website:http://www.np-chem.com
Contact:0086-25-52346877
Address:199, Jian Ye Road, Nanjing, China
Quzhou Aokai Chemical Co., Ltd.
Contact:86-570-3032832
Address:NO.16 , Laodong Road,Quzhou City, Zhejiang Province,China
Doi:10.1016/j.nucmedbio.2018.11.002
(2019)Doi:10.1021/om4000192
(2013)Doi:10.1016/0022-328X(84)80668-3
(1984)Doi:10.1016/S0031-9422(00)82220-7
(1980)Doi:10.1246/cl.2012.1619
(2012)Doi:10.1016/S0040-4039(01)98843-4
(1968)
