Aminomethylation of Oxabenzonorbornadienes via the Merger of Photoredox and Nickel Catalysis

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...

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Bibliographic Details
Published in:Organic letters 2020-03, Vol.22 (6), p.2442-2447
Main Authors: Diallo, Abdoul G, Roy, David, Gaillard, Sylvain, Lautens, Mark, Renaud, Jean-Luc
Format: Article
Language:English
Subjects:
Catalysis
Chemical Sciences
Material chemistry
Organic chemistry
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Summary: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 π-allyl intermediate.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c00593