Aminomethylation of Oxabenzonorbornadienes via the Merger of Photoredox and Nickel Catalysis

被引：18
|
作者：
Diallo, Abdoul G. [1 ]
Roy, David [1 ]
Gaillard, Sylvain [1 ]
Lautens, Mark [2 ]
Renaud, Jean-Luc [1 ]
机构：
[1] Normandie Univ, CNRS, UNICAEN, LCMT,ENSICAEN, F-14000 Caen, France
[2] Univ Toronto, Dept Chem, Davenport Chem Labs, Toronto, ON MSS 3H6, Canada
来源：
ORGANIC LETTERS | 2020年 / 22卷 / 06期
关键词：
RING-OPENING REACTIONS; OXABICYCLIC ALKENES; CARBON-CARBON; BORONIC ACIDS; LIGHT; RADICALS; FUNCTIONALIZATION; GENERATION; PHOTOCHEMISTRY; OPPORTUNITIES;
D O I：
10.1021/acs.orglett.0c00593
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The first aminomethylation of oxabenzonorbornadienes using dual photoredox/nickel catalysis has been disclosed. This cascade reaction allowed the preparation of the cis-aminomethyl dihydronaphthalenols without any prefunctionalization or any use of nucleophilic organometallic species. The control of the regio- and stereoselectivity might be explained by a sequence involving insertion of nickel(0) into the C-O bond followed by the formation of a pi-allyl intermediate.
引用
收藏
页码：2442 / 2447
页数：6
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