Iridium-Catalyzed Hydroiodination and Formal Hydroamination of Olefins with N-Iodo Reagents and Molecular Hydrogen: An Umpolung Strategy

Yang, Huaxin1; Zhou, Yang1; Zhang, Zhihan1; Wen, Jialin1,2; Zhang, Xumu1

2022-03-11

10.1021/acs.orglett.2c00392

ORGANIC LETTERS   影响因子和分区

1523-7060

1523-7052

We herein report a convenient method to convert olefins to organic iodides and amines using an Ir/ZhaoPhos catalyst, molecular hydrogen, and an electrophilic iodine(I) reagent. High yields and regioselectivities were obtained under mild conditions. In addition, basic workup with potassium carbonate leads to C-N products. Control experiments and DFT calculations tentatively excluded the pathway involving the in situ formation of HL Instead, a catalytic cycle involving the hydrogenation of the haliranium ion intermediate was proposed.

SCI

英语

NI期刊

第一 ; 通讯

National Natural Science Foundation of China[21801118] ; Guangdong Provincial Key Laboratory of Catalysis[2020B121201002]

Chemistry

Chemistry, Organic

WOS:000770063700017

AMER CHEMICAL SOC

CHEMISTRY

Web of Science

1.Southern Univ Sci & Technol, Dept Chem, Guangdong Prov Key Lab Catalysis, Shenzhen 518005, Peoples R China
2.Southern Univ Sci & Technol, Acad Adv Interdisciplinary Studies, Shenzhen 518005, Peoples R China

Yang, Huaxin,Zhou, Yang,Zhang, Zhihan,et al. Iridium-Catalyzed Hydroiodination and Formal Hydroamination of Olefins with N-Iodo Reagents and Molecular Hydrogen: An Umpolung Strategy[J]. ORGANIC LETTERS,2022,24(9).

Yang, Huaxin,Zhou, Yang,Zhang, Zhihan,Wen, Jialin,&Zhang, Xumu.(2022).Iridium-Catalyzed Hydroiodination and Formal Hydroamination of Olefins with N-Iodo Reagents and Molecular Hydrogen: An Umpolung Strategy.ORGANIC LETTERS,24(9).

Yang, Huaxin,et al."Iridium-Catalyzed Hydroiodination and Formal Hydroamination of Olefins with N-Iodo Reagents and Molecular Hydrogen: An Umpolung Strategy".ORGANIC LETTERS 24.9(2022).