From Carboxytelomerization of 1,3-Butadiene to Linear α,ω-C10 -Diester Combinatoric Approaches for an Efficient Synthetic Route.
Chemistry
; 24(9): 2264-2269, 2018 Feb 09.
Article
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| MEDLINE
| ID: mdl-29266442
ABSTRACT
Two novel reaction pathways were tested to synthesize the linear α,ω-C10 -diester exclusively from three basic reagents 1,3-butadiene, carbon monoxide and methanol. Therefore, carboxytelomerization of 1,3-butadiene and methanol was merged with methoxycarbonylation in two different ways to obtain highly linear C10 -diester. Through a palladium-based and -assisted tandem catalytic system, 22 % yield of the desired C10 -diester was obtained without isolating the intermediates. Subsequently, the limitations of the novel assisted tandem catalytic concept were uncovered and based on that, a two-step reaction regime was established. By optimization of the carboxytelomerization, the C9 -monoester as intermediate could be formed in nearly quantitative yields and excellent linearity. In a second reaction step, the isolated monoester was successfully converted by methoxycarbonylation into the desired linear C10 -diester in overall yields up to 84 %.
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1
Colección:
01-internacional
Base de datos:
MEDLINE
Idioma:
En
Revista:
Chemistry
Asunto de la revista:
QUIMICA
Año:
2018
Tipo del documento:
Article
País de afiliación:
Alemania