Dehydration of Aldoximes Using PhSe(O)OH as the Pre-Catalyst in Air

被引:102
作者
Zhang, Xu [1 ]
Sun, Jingjing [1 ]
Ding, Yuanhua [1 ]
Yu, Lei [1 ]
机构
[1] Yangzhou Univ, Sch Chem & Chem Engn, Jiangsu Coinnovat Ctr Prevent & Control Important, Jiangsu Key Lab Zoonosis, Yangzhou 225002, Jiangsu, Peoples R China
关键词
BAEYER-VILLIGER OXIDATION; ORGANOSELENIUM COMPOUNDS; HYDROGEN-PEROXIDE; SELENIUM; AMINATION; ALKENES; ACCESS; DIHYDROXYLATION; CYCLOHEXENE; CYCLIZATION;
D O I
10.1021/acs.orglett.5b03011
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
PhSe(O)OH was found to be a good pre-catalyst for aldoxime dehydrations in open air. Compared with the previously reported (PhSe)(2)-H2O2 system, it is more stable and milder, affording broader application scopes due to a higher functional group tolerance. The control experiments for mechanism study disclosed that air was the key factor for the reaction to maintain enough concentration of PhSeOH, which should be the real catalytic species.
引用
收藏
页码:5840 / 5842
页数:3
相关论文
共 38 条
[1]   Recent developments in sulfur- and selenium-catalyzed oxidative and isohypsic functionalization reactions of alkenes [J].
Breder, Alexander ;
Ortgies, Stefan .
TETRAHEDRON LETTERS, 2015, 56 (22) :2843-2852
[2]   Iron-Catalyzed Cyclization of Alkynols with Diorganyl Diselenides: Synthesis of 2,5-Dihydrofuran, 3,6-Dihydro-2H-pyran, and 2,5-Dihydro-1H-pyrrole Organoselanyl Derivatives [J].
Casola, Kamila K. ;
Back, Davi F. ;
Zeni, Gilson .
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (15) :7702-7712
[3]   C2-Symmetric Cyclic Selenium-Catalyzed Enantioselective Bromoaminocyclization [J].
Chen, Feng ;
Tan, Chong Kiat ;
Yeung, Ying-Yeung .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (04) :1232-1235
[4]  
Cresswell AJ, 2015, NAT CHEM, V7, P146, DOI [10.1038/NCHEM.2141, 10.1038/nchem.2141]
[5]   Organoselenium-Catalyzed, Hydroxy-Controlled Regio- and Stereoselective Amination of Terminal Alkenes: Efficient Synthesis of 3-Amino Allylic Alcohols [J].
Deng, Zhimin ;
Wei, Jialiang ;
Liao, Lihao ;
Huang, Haiyan ;
Zhao, Xiaodan .
ORGANIC LETTERS, 2015, 17 (08) :1834-1837
[6]   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
[7]   Synthesis of Heterocycles via Electrophilic Cyclization of Alkynes Containing Heteroatom [J].
Godoi, Benhur ;
Schumacher, Ricardo F. ;
Zeni, Gilson .
CHEMICAL REVIEWS, 2011, 111 (04) :2937-2980
[8]  
Karig S.-I., 1985, J ORG CHEM, V50, P2968
[9]   MECHANISM OF THE HYDROLYSIS OF ORTHO-NITROBENZENESELENENIC AND ORTHO-BENZOYLBENZENESELENENIC ANHYDRIDES [J].
KICE, JL ;
MCAFEE, F ;
SLEBOCKATILK, H .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (17) :3100-3106
[10]   THE ANHYDRIDE STRUCTURE OF SEVERAL PREVIOUSLY REPORTED STABLE ARENESELENENIC ACIDS [J].
KICE, JL ;
MCAFEE, F ;
SLEBOCKATILK, H .
TETRAHEDRON LETTERS, 1982, 23 (33) :3323-3326