Functionally Diverse Nucleophilic Trapping of Iminium Intermediates Generated Utilizing Visible Light

被引：352
作者：
Freeman, David B. [1 ]
Furst, Laura [1 ]
Condie, Allison G. [1 ]
Stephenson, Corey R. J. [1 ]
机构：
[1] Boston Univ, Dept Chem, Boston, MA 02215 USA
来源：
ORGANIC LETTERS | 2012年 / 14卷 / 01期
关键词：
SP(3) C-H; BOND-DISSOCIATION ENERGIES; LOW-VALENT RUTHENIUM; PHOTOREDOX CATALYSIS; MOLECULAR-OXYGEN; RADICAL CATIONS; TERTIARY-AMINES; BASE CATALYSTS; NITROGEN ATOM; LEWIS-ACID;
D O I：
10.1021/ol202883v
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Our previous studies into visible-light-mediated aza-Henry reactions demonstrated that molecular oxygen played a vital role in catalyst turnover as well as the production of base to facilitate the nucleophilic addition of nitroalkanes. Herein, improved conditions for the generation of iminium Ions from tetrahydroisoquinolines that allow for versatile nucleophilic trapping are reported. The new conditions provide access to a diverse range of functionality under mild, anaerobic reaction conditions as well as mechanistic insights into the photoredox cycle.
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页码：94 / 97
页数：4
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