Pd-Catalyzed decarboxylative cross-coupling reactions of epoxides with α,β-unsaturated carboxylic acids

• Published in: Chemical communications (Cambridge, England) Vol. 55; no. 74; pp. 11123 - 11126
• Main Authors: Lu, Xiao-Yu, Li, Jin-Song, Wang, Shi-Qun, Zhu, Yu-Jing, Li, Yue-Ming, Yan, Lu-Yu, Li, Jia-Mei, Wang, Jin-Yu, Zhou, Hai-Pin, Ge, Xiu-Tao
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 21.09.2019; Royal Society of Chemistry
• Subjects: Acids; Alcohols; Carboxylic acids; Chemical reactions; Chemistry; Chemistry, Multidisciplinary; Coupling (molecular); Cross coupling; Organic chemistry; Palladium; Physical Sciences; Science & Technology; Substrates; HECK-TYPE REACTION; 1,3-DIENES; ALKYLATION; HOMOALLYLIC ALCOHOLS; ALPHA; REDOX-ACTIVE ESTERS; STEREOSELECTIVE-SYNTHESIS; ACCESS
• ISSN: 1359-7345; 1364-548X
• DOI: 10.1039/c9cc04795f

A Pd-catalyzed decarboxylative cross-coupling of α,β-unsaturated carboxylic acids with cyclic and acyclic epoxides has been developed. Both β-monosubstituted and β-disubstituted unsaturated carboxylic acids, as well as conjugated diene unsaturated carboxylic acids are suitable reaction substrates. Substituted homoallylic alcohols were obtained in moderate to good yields. The product was obtained as a mixture of diastereomers favoring the anti diastereomer of the cyclic epoxides. This work provides a method for the modification of complex organic molecules containing α,β-unsaturated carboxylic acids. A Pd-catalyzed decarboxylative cross-coupling of α,β-unsaturated carboxylic acids with cyclic and acyclic epoxides has been developed.