文献类型：期刊文献

英文题名：Amine-Catalyzed Highly Regioselective and Stereoselective C(sp2)-C(sp2) Cross-Coupling of Naphthols with trans-,-Unsaturated Aldehydes

作者：Hu, Yang[1,2,3];Ma, Yueyue[1,2,3];Sun, Rengwei[1,2,3];Yu, Xinhong[1,2,3];Xie, Hexin[1,2,3];Wang, Wei[1,2,3,4]

机构：[1]E China Univ Sci & Technol, Shanghai Key Lab New Drug Design, Shanghai 200237, Peoples R China;[2]E China Univ Sci & Technol, Sch Pharm, Shanghai 200237, Peoples R China;[3]E China Univ Sci & Technol, State Key Lab Bioengn Reactors, Shanghai 200237, Peoples R China;[4]Univ New Mexico, Dept Chem & Chem Biol, Albuquerque, NM 87131 USA

年份：2015

卷号：10

期号：9

起止页码：1859

外文期刊名：CHEMISTRY-AN ASIAN JOURNAL

收录：;EI(收录号：20153501221626);WOS:【SCI-EXPANDED(收录号:WOS:000360589300006)】；

基金：Research support from the National Natural Science Foundation of China (20972051 and 21476078, X.-H.Y.; 21472048, H.-X. X and 21372073, W. W.), the Science and Technology Commission of Shanghai Municipality (12431900900, 12431900902, 08431901800 and 08430703900, X.-H. Y.), the Fundamental Research Funds for the Central Universities (H.-X. X), the National Science Foundation (CHE-1057569, W. W.) and the China 111 Project (Grant B07023, W. W.) are gratefully acknowledged.

语种：英文

外文关键词：cascade reaction; cross-coupling; metal-free; organocatalysis; -naphtholylation

摘要：A metal-free C(sp(2))-C(sp(2)) cross-coupling approach to highly congested (E)--naphtholylenals from simple naphthols and enals is described. The mild reaction conditions with pyridine hydrobromideperbromide (PHBP) as the bromination reagent in the presence of piperidine or diphenylprolinol trimethylsilyl (TMS) ether as promoters enable the process in good yields and with high chemoselectivity, regioselectivity, and stereoselectivity. The process involves an unprecedented pathway of in situ regioselective 4-bromination of 1-naphthols and the subsequent unusual aromatic nucleophilic substitution of the resulting 4-bromo-1-naphthols with the -C(sp(2)) of enals through a Michael-type Friedel-Crafts alkylation-dearomatization followed by a cyclopropanation ring-opening cascade process. The noteworthy features of this strategy are highlighted by the highly efficient creation of a C(sp(2))-C(sp(2)) bond from readily available unfunctionalized naphthols and enals catalyzed by non-metal, readily available cyclic secondary amines under mild reaction conditions.