PhI(OAc)2-Mediated Dihalogenative Cyclization of 1,6-Enyne with Lithium Halide

被引:24
作者
Dong, Ming [1 ]
Wang, Danfeng [1 ]
Tong, Xiaofeng [1 ]
机构
[1] Changzhou Univ, Sch Petrochem Engn, Jiangsu Key Lab Adv Catalyt Mat & Technol, Changzhou 213164, Peoples R China
关键词
CATALYZED OXIDATIVE CYCLIZATION; ANNULATION; ENYNES; N-ENYNES; CYCLOISOMERIZATION; FUNCTIONALIZATION; CARBOCYCLIZATION; ALKYNES;
D O I
10.1021/acs.orglett.1c00987
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The dihalogenative cyclization of 1,6-enyne with the assistance of PhI(OAc)(2) and lithium halide is presented. A plausible radical mechanism is proposed, which consists of addition of halogen radical to alkene, 5-exo-dig radical cyclization of enyne and halogenation via radical coupling. The alkenyl- and alkyl-halide groups in the resulted pyrrolidine products have been demonstrated to be facile handles for further transformations.
引用
收藏
页码:3588 / 3592
页数:5
相关论文
共 52 条
[1]   Advances in Iodine(III)-Mediated Halogenations: A Versatile Tool to Explore New Reactivities and Selectivities [J].
Arnold, Andreas M. ;
Ulmer, Anna ;
Gulder, Tanja .
CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (26) :8728-8739
[2]   The behavior of 1,n-enynes in the presence of transition metals [J].
Aubert, C ;
Buisine, O ;
Malacria, M .
CHEMICAL REVIEWS, 2002, 102 (03) :813-834
[3]   Arylsulfonyl Radical Triggered 1,6-Enyne Cyclization: Synthesis of γ-Lactams Containing Alkenyl C-X Bonds [J].
Cao, Xia ;
Cheng, Xiao ;
Xuan, Jun .
ORGANIC LETTERS, 2018, 20 (02) :449-452
[4]   Rhodium-Catalyzed Carbocyclization and Chlorosulfonylation of 1,6-Enynes with Sulfonyl Chlorides [J].
Chen, Chen ;
Su, Jianhua ;
Tong, Xiaofeng .
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (16) :5014-5018
[5]   A Practical Aryliodine(I/III) Catalysis for the Vicinal Diamination of Styrenes [J].
Cots, Eric ;
Flores, Andrea ;
Martin Romero, R. ;
Muniz, Kilian .
CHEMSUSCHEM, 2019, 12 (13) :3028-3031
[6]   RhI-Catalyzed Cyclizative Addition Reaction of 1,6-Enyne and Sulfonyl Chloride by Carbophilic Activation [J].
Dang, Mengyao ;
Hou, Longlei ;
Tong, Xiaofeng .
CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (23) :7734-7738
[7]   Rhodium-catalyzed cycloaddition of 1,6-enynes with 2-bromophenylboronic acids: synthesis of a multi-substituted dihydronaphthalene scaffold [J].
Fang, Xianjie ;
Li, Chaolong ;
Tong, Xiaofeng .
CHEMICAL COMMUNICATIONS, 2009, (35) :5311-5313
[8]   Enantioselective Iodine(I/III) Catalysis in Organic Synthesis [J].
Flores, Andrea ;
Cots, Eric ;
Berges, Julien ;
Muniz, Kilian .
ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (01) :2-25
[9]   Effect of substituents on the structure of the vinyl radical: Calculations and experiments [J].
Galli, C ;
Guarnieri, A ;
Koch, H ;
Mencarelli, P ;
Rappoport, Z .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (12) :4072-4077
[10]   Structurally Defined Molecular Hypervalent Iodine Catalysts for Intermolecular Enantioselective Reactions [J].
Haubenreisser, Stefan ;
Woeste, Thorsten H. ;
Martinez, Claudio ;
Ishihara, Kazuaki ;
Muniz, Kilian .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (01) :413-417