期刊
SCIENCE
卷 369, 期 6503, 页码 557-+出版社
AMER ASSOC ADVANCEMENT SCIENCE
DOI: 10.1126/science.abb4129
关键词
-
资金
- NSERC Canada [RGPIN-2019-06050, RGPAS-2019-00051]
- Canadian Foundation for Innovation [IOF 32691]
- University of Alberta
- Killam Trusts
Many classical and emerging methodologies in organic chemistry rely on carbon dioxide (CO2) extrusion to generate reactive intermediates for bond-forming events. Synthetic reactions that involve the microscopic reverse-the carboxylation of reactive intermediates-have conventionally been undertaken using very different conditions. We report that chemically stable C(sp(3)) carboxylates, such as arylacetic acids and malonate half-esters, undergo uncatalyzed reversible decarboxylation in dimethylformamide solution. Decarboxylation-carboxylation occurs with substrates resistant to protodecarboxylation by Bronsted acids under otherwise identical conditions. Isotopically labeled carboxylic acids can be prepared in high chemical and isotopic yield by simply supplying an atmosphere of (CO2)-C-13 to carboxylate salts in polar aprotic solvents. An understanding of carboxylate reactivity in solution enables conditions for the trapping of aldehydes, ketones, and alpha,beta-unsaturated esters.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据