发明名称 Production method for 2-alkenylamine compound
摘要 Provided is a method for producing a 2-alkenylamine compound efficiently and at low cost, using a primary or secondary amine compound and a 2-alkenyl compound as the starting materials therefor. The 2-alkenylamine compound is produced by adding Bronsted acid when 2-alkenylating by reacting the primary or secondary amine compound with the 2-alkenyl compound, and 2-alkenylating in the presence of a catalyst comprising a complexing agent and a transition metal precursor stabilized by a monovalent anionic five-membered conjugated diene.
申请公布号 US9440907(B2) 申请公布日期 2016.09.13
申请号 US201214237758 申请日期 2012.08.29
申请人 SHOWA DENKO K.K.;NATIONAL UINVERSITY CORPORATION NAGOYA UNIVERSITY 发明人 Ishibashi Yoshitaka;Fukumoto Naoya;Kitamura Masato
分类号 C07C209/68;C07C209/16;C07C209/18;B01J31/22 主分类号 C07C209/68
代理机构 Sughrue Mion, PLLC 代理人 Sughrue Mion, PLLC
主权项 1. A method for producing a 2-alkenylamine compound by reacting a primary or secondary amine compound with a 2-alkenyl compound in the presence of a catalyst, wherein the catalyst is a transition metal complex which is a reaction product of a complexing agent having a nitrogen coordination site and an oxygen coordination site bidentate-coordinated to a transition metal atom in the molecule and a transition metal precursor having a monovalent anionic five-membered ring-conjugated diene as a ligand in the molecule, and wherein a Bronsted acid selected from the group consisting of halogenated hydrogens, sulfuric acid, sulfonic acids, oxo acids of phosphorus, carboxylic acids, and boric acids is added, wherein the complexing agent is an α-imino acid type ligand compound of the following formula (2): wherein R6 to R9 are, independently from each other, a hydrogen atom, a C1 to C10 alkyl group, a C3 to C12 cycloalkyl group, a C6 to C10 aryl group, an alkyl-substituted silyl group, said substituent having a total of 1 to 30 carbons, or an aryl-substituted silyl group, said substituent having a total of 6 to 30 carbons, or R6 and R7, R7 and R8, R8 and R9, R6 and R8, R6 and R9, or R7 and R9 may bind to each other to form a saturated or unsaturated 4 to 8-membered ring, wherein the monovalent anionic 5-membered ring-conjugated diene has a conjugatable monovalent anionic structure, wherein the anion is conjugated to the binding carbons of R10 to R30, the structure of any of the following formulae (3-1), (3-2) and (3-3): wherein R10 to R30 are, independently from each other, a hydrogen atom, a C1 to C10 alkyl group, a C3 to C12 cycloalkyl group, a C6 to C10 aryl group, an alkyl-substituted silyl group, said substituent having a total of 1 to 30 carbons, or an aryl-substituted silyl group, said substituent having a total of 6 to 30 carbons, and groups binding to adjacent two carbon atoms on the ring may bind to each other to form a saturated or unsaturated 4 to 8-membered ring together with the adjacent two carbon atoms, wherein the 2-alkenyl compound is a compound of the following formula (1): wherein R1, R2, R3, R4 and R5 are, independently from each other, a hydrogen atom, a C1 to C10 alkyl group, a C2 to C10 alkenyl group, a C1 to C10 alkoxy group, a C3 to C12 cycloalkyl group, a C3 to C12 cycloalkenyl group, an acetoxy group, or a C6 to C10 aryl group; and X is a substituent selected from the group consisting of —NO2, HO—, RO—, RS(O)2O—, RCOO—, and ROCOO— wherein R is a C1 to C30 organic group, and wherein the Bronsted acid is used at an amount of 1 to 20 moles per mole of the primary or secondary amine compound.
地址 Tokyo JP