期刊
CHEMSUSCHEM
卷 14, 期 9, 页码 2084-2092出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cssc.202100262
关键词
CO2; cyclic carbonates; green chemistry; Grignard reagents; organolithium compounds
资金
- Spanish MINECO [CTQ2016-75986-P, CTQ2016-81797-REDC, RED2018-102387-T]
- PhosAgro/UNESCO/IUPAC
- Gobierno del Principado de Asturias
- EU
- Junta de Comunidades de Castilla la Mancha
- EU through the European Regional Development Fund (ERDF) [SBPLY/19/180501/000137]
- MINECO, Spain [CTQ2016-81797-REDC, RED2018-102387-T, CTQ2017-84131-R]
- Ministerio de Educacion, Cultura y Deporte (MECD) [FPU15/01772]
The rapid addition of highly polar organometallic reagents to cyclic carbonates has been studied, allowing for the synthesis of highly substituted tertiary alcohols, beta-hydroxy esters, or symmetric ketones without the need for isolation or purification of any reaction intermediates.
Fast addition of highly polar organometallic reagents (RMgX/RLi) to cyclic carbonates (derived from CO2 as a sustainable C1 synthon) has been studied in 2-methyltetrahydrofuran as a green reaction medium or in the absence of external volatile organic solvents, at room temperature, and in the presence of air/moisture. These reaction conditions are generally forbidden with these highly reactive main-group organometallic compounds. The correct stoichiometry and nature of the polar organometallic alkylating or arylating reagent allows straightforward synthesis of: highly substituted tertiary alcohols, beta-hydroxy esters, or symmetric ketones, working always under air and at room temperature. Finally, an unprecedented one-pot/two-step hybrid protocol is developed through combination of an Al-catalyzed cycloaddition of CO2 and propylene oxide with the concomitant fast addition of RLi reagents to the in situ and transiently formed cyclic carbonate, thus allowing indirect conversion of CO2 into the desired highly substituted tertiary alcohols without need for isolation or purification of any reaction intermediates.
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