N-Iodosuccinimide: A Highly Effective Regioselective Reagent for Iodoesterification of Alkenes

被引:11
作者
Reddy, Aleti R. [1 ]
Sangwan, Payare L. [1 ]
Chinthakindi, Praveen K. [1 ]
Farooq, Saleem [1 ]
Siddaiah, Vidavalur [2 ]
Koul, Surrinder [1 ]
机构
[1] CSIR Indian Inst Integrat Med, Bioorgan Chem Div, Jammu 180001, Tawi, India
[2] Andhra Univ, Dept Organ Chem Food Drugs & Water, Visakhapatnam 530003, Andhra Pradesh, India
关键词
Alkenes; N-Iodosuccinimide (NIS); Iodohydrins; Iodoesterification; ODORLESS BENZENETHIOLS; BENZENESULFINIC ACID; AMINOHALOGENATION; BROMINATION; IODOHYDRINS; DERIVATIVES; HALOHYDRINS; CONVERSION; OLEFINS; AMINES;
D O I
10.1002/hlca.201200383
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A rapid, convenient, and efficient method has been achieved for regioselective iodoesterification of alkenes with aliphatic and aromatic acids, and protected amino acids in the presence of N-iodosuccinimide (NIS) in nearly quantitative yields. Optically enriched iodohydrins have been achieved by LiAlH4 (LAH) reduction of diastereoisomeric iodo esters.
引用
收藏
页码:1313 / 1324
页数:12
相关论文
共 50 条
[1]   Intramolecular aminochalcogenation and diamination of alkenes employing N-iodosuccinimide [J].
Zhang, Jun ;
Zhang, Xuejun ;
Wu, Weijie ;
Zhang, Gengtao ;
Xu, Sheng ;
Shi, Min .
TETRAHEDRON LETTERS, 2015, 56 (12) :1505-1509
[2]   Regioselective carboiodination of styrenes: N-iodosuccinimide affords complete reaction regioselectivity [J].
Goto, Mayuki ;
Maejima, Saki ;
Yamaguchi, Eiji ;
Itoh, Akichika .
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 9 (02) :210-213
[3]   Iodosulfonation of alkenes with benzenesulfinic acid -: N-iodosuccinimide -: Facile preparation of α,β-unsaturated sulfones [J].
Wolff, Russell R. ;
Basava, Vikram ;
Giuliano, Robert M. ;
Boyko, Walter J. ;
Schauble, J. Herman .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 2006, 84 (04) :667-675
[4]   Intramolecular diamination and alkoxyamination of alkenes with N-sulfonyl ureas employing N-iodosuccinimide [J].
Li, Hao ;
Widenhoefer, Ross A. .
TETRAHEDRON, 2010, 66 (26) :4827-4831
[5]   N-Iodosuccinimide (NIS) in Direct Aromatic Iodination [J].
Bergstrom, Maria ;
Suresh, Ganji ;
Naidu, Veluru Ramesh ;
Unelius, C. Rikard .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (22) :3234-3239
[6]   Regioselective 1,2-additions of alcohols to allenamides mediated by N-Iodosuccinimide: Synthesis of N,O-aminals [J].
Yuan, Xiao ;
Man, Xi Jia Ai Ti Re He ;
Li, Xiao-Xiao ;
Zhao, Zhi-Gang .
TETRAHEDRON, 2018, 74 (39) :5674-5682
[7]   Metal-Free,N-Iodosuccinimide-Induced Regioselective Iodophosphoryloxylation of Alkenes with P(O)-OH Bonds [J].
Xiong, Biquan ;
Xu, Shipan ;
Zhu, Yu ;
Yao, Lei ;
Zhou, Congshan ;
Liu, Yu ;
Tang, Ke-Wen ;
Wong, Wai-Yeung .
CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (43) :9556-9560
[8]   Dichloroiodoisocyanuric Acid: A New Reagent for Regioselective Coiodination of Alkenes and Iodination of Activated Arenes [J].
da Silva Ribeiro, Rodrigo ;
Esteves, Pierre M. ;
de Mattos, Marcio C. S. .
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2012, 23 (02) :228-235
[9]   An Intramolecular C(sp2)-H Amidation Using N-Iodosuccinimide [J].
Alam, Md Toufique ;
Maiti, Saikat ;
Mal, Prasenjit .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (30) :4178-4186
[10]   Intramolecular C-H Amination of N-Alkylsulfamides by tert-Butyl Hypoiodite or N-Iodosuccinimide [J].
Kiyokawa, Kensuke ;
Jou, Keisuke ;
Minakata, Satoshi .
CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (56) :13971-13976