文献类型：期刊文献

英文题名：Pd-Catalyzed Debenzylation and Deallylation of Ethers and Esters with Sodium Hydride

作者：Mao, Yujian[1,2];Liu, Ye[1,2];Hu, Yanwei[1,2];Wang, Liang[3];Zhang, Shilei[1,2];Wang, Wei[4,5,6]

机构：[1]Soochow Univ, Jiangsu Key Lab Neuropsychiat Dis, 199 Renai Rd, Suzhou 215123, Jiangsu, Peoples R China;[2]Soochow Univ, Coll Pharmaceut Sci, 199 Renai Rd, Suzhou 215123, Jiangsu, Peoples R China;[3]Qingdao Agr Univ, Coll Chem & Pharmaceut Sci, Qingdao 266109, Peoples R China;[4]East China Univ Sci & Technol, Sch Pharm, State Key Lab Bioengn Reactor, Shanghai 200237, Peoples R China;[5]East China Univ Sci & Technol, Sch Pharm, Shanghai Key Lab New Drug Design, Shanghai 200237, Peoples R China;[6]Univ New Mexico, Dept Chem & Chem Biol, Albuquerque, NM 87131 USA

年份：2018

卷号：8

期号：4

起止页码：3016

外文期刊名：ACS CATALYSIS

收录：;EI(收录号：20181505002897);WOS:【SCI-EXPANDED(收录号:WOS:000430154100045)】；

基金：This work was supported by the National Natural Science Foundation of China (21202112, 21738002), Suzhou Science and Technology Project (Grant No. ZXY201435), PAPD (A Project Funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions), the Natural Science Foundation of Shandong Province (ZR2016BM07), and the Qingdao Special Research Foundation of Science and Technology (16-1-2-29 nsh).

语种：英文

外文关键词：sodium hydride; palladium; reduction; debenzylation; deallylation

摘要：Herein we demonstrate simply that the addition of Pd(OAc)(2) as a promotor switches the reactivity of a commonly used base NaH to a nucleophilic reductant. The reactivity is engineered into a palladium-catalyzed reductive debenzylation and deallylation of aryl ethers and esters. This operationally simple, mild protocol displays a broad substrate scope and a broad spectrum of functional group tolerance (>50 examples) and high chemoselectivity toward aryl ethers over aliphatic structures. Moreover, the dual reactivity of NaH as a base and a reductant is demonstrated in efficient synthetic elaboration.