Ring-opening selenation of cyclobutanols: synthesis of γ-selenylated alkyl ketones through C-C bond cleavage

被引：37
作者：
Wang, Mingyang [1 ]
Wu, Zhen [1 ]
Zhu, Chen [1 ,2 ]
机构：
[1] Soochow Univ, Key Lab Organ Synth Jiangsu Prov, Coll Chem Chem Engn & Mat Sci, 199 Ren Ai Rd, Suzhou 215123, Jiangsu, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, Shanghai 200032, Peoples R China
来源：
ORGANIC CHEMISTRY FRONTIERS | 2017年 / 4卷 / 03期
基金：
中国国家自然科学基金;
关键词：
CATALYZED ASYMMETRIC ARYLATION; REGIOSPECIFIC SYNTHESIS; TERT-CYCLOBUTANOLS; REGIOSELECTIVE SYNTHESIS; FLUORINATED KETONES; MICHAEL ADDITION; MANGANESE; ACTIVATION; CYCLOALKANOLS; CHLORINATION;
D O I：
10.1039/c6qo00744a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient and practical manganese-mediated ring-opening selenation of cyclobutanols is disclosed. The transformation has broad functionality tolerance, producing a variety of gamma-selenylated alkyl ketones in synthetically useful yields. Mechanistically, the radical-promoted regioselective cyclic C-C bond cleavage and sp(3) C-Se bond formation are involved.
引用
收藏
页码：427 / 430
页数：4
相关论文
共 64 条
[1]  
[Anonymous], 1999, ORGANOSELENIUM CHEM
[2]  
[Anonymous], ORGANOSELENIUM CHEM
[3]  
Baldwin J. E., 1986, SELENIUM REAGENTS IN
[4]   "On-Water" Michael-Type Addition Reactions Promoted by PhSeZnCl [J].
Battistelli, Benedetta ;
Lorenzo, Testaferri ;
Tiecco, Marcello ;
Santi, Claudio .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (10) :1848-1851
[5]   Synthesis of γ-halogenated ketones via the Ce(IV)-mediated oxidative coupling of cyclobutanols and inorganic halides [J].
Casey, Brian M. ;
Eakin, Cynthia A. ;
Flowers, Robert A., II .
TETRAHEDRON LETTERS, 2009, 50 (12) :1264-1266
[6]   Regiospecific synthesis of distally chlorinated ketones via C-C bond cleavage of cycloalkanols [J].
Fan, Xuefeng ;
Zhao, Huijun ;
Yu, Jiajia ;
Bao, Xiaoguang ;
Zhu, Chen .
ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (02) :227-232
[7]   Recent Advances in the Synthesis of Distal Fluorinated Ketones [J].
Fan Xuefeng ;
Zhao Huijun ;
Zhu Chen .
ACTA CHIMICA SINICA, 2015, 73 (10) :979-983
[8]  
Flores-Gaspar A., 2013, SYNTHESIS-STUTTGART, P563
[9]   Green Chemistry with Selenium Reagents: Development of Efficient Catalytic Reactions [J].
Freudendahl, Diana M. ;
Santoro, Stefano ;
Shahzad, Sohail A. ;
Santi, Claudio ;
Wirth, Thomas .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (45) :8409-8411
[10]   Ring Openings of tert-Cyclobutanols: New Strategy towards the Synthesis of γ-Substituted Ketones via C-C Bond Cleavage [J].
Hong, Yan ;
Chen, Zhu .
PROGRESS IN CHEMISTRY, 2016, 28 (01) :1-8
1234567