New aminoborane derivatives useful as borylating agents, e.g. for preparing arylboratranes, 2-aryl-5,5-dimethyl-1,3,2-dioxaborinanes, arylboronic acids and B,B-diaryl-aminoboranes

摘要

Aminoborane derivatives (I) are new. Compounds of formula (I) are new: A-BH-NR1R2 (I) R1, R2 = 2-20C alkyl, 3-20C cycloalkyl or aralkyl, or R1+R2 is alkylene, and preferably the groups are chiral; A = aryl, heteroaryl, vinyl, dienyl, polyenyl or alkynyl, all optionally substituted with alkyl, alkoxy, amino, dialkylamino, halo, CN, ester, amide, (thio)acetal, (thio)ketal, trialkylsilyl and dialkoxyboryl. Independent claims are also included for: (i) a process for preparing compounds (I); (ii) production of arylboratranes by reacting (I) with dihydroxyethylamines; (iii) production of 2-aryl-5,5-dimethyl-1,3,2-dioxaborinanes by reacting (I) with 2,2-dimethyl-1,4-propanediol; (iv) production of arylboronic acids by reaction (I) with excess methanol and hydrolyzing the resulting aryldimethoxyborane; (v) production of B,B-diaryl-aminoboranes by reacting (I) with A-X (not defined) in the presence of a zero-valent palladium (Pd(0)) catalyst and a base; (vi) production of compounds A-A by reacting (I) with A-Z (not defined) in the presence of a Pd(0) catalyst, a base and water.