Palladium-catalyzed hydroamination of vinylidenecyclopropane-diester with pyrroles and indoles: an approach to azaaromatic vinylcyclopropanes

A new method for the synthesis of azaaromatic vinylcyclopropanes (VCPs) has been disclosed in this paper by using pyrrole or indole derivatives as nucleophilic reagents to react with vinylidenecyclopropane-diesters (VDCP-diesters) in the presence of a Pd catalyst, a phosphine ligand and a base under...

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Published inChemical communications (Cambridge, England) Vol. 58; no. 71; pp. 9926 - 9929
Main Authors Yang, Ze-ren, Zhang, Bo, Long, Yong-jie, Shi, Min
Format Journal Article
LanguageEnglish
Published Cambridge Royal Society of Chemistry 01.09.2022
Subjects
Deuterium
Diesters
Indoles
Palladium
Phosphines
Pyrroles
Reaction mechanisms
Reagents
Substrates
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Summary:A new method for the synthesis of azaaromatic vinylcyclopropanes (VCPs) has been disclosed in this paper by using pyrrole or indole derivatives as nucleophilic reagents to react with vinylidenecyclopropane-diesters (VDCP-diesters) in the presence of a Pd catalyst, a phosphine ligand and a base under mild conditions in up to 98% yield with a reasonable substrate scope. This reaction is one of the few examples of hydroamination at electron-rich allene's β-position. A plausible reaction mechanism has also been proposed through a zwitterionic π-propargyl N -palladium species according to the previous work and the obtained deuterium labeling experimental result. A new method for the synthesis of azaaromatic vinylcyclopropanes (VCPs) via palladium and Lewis acid catalyzed hydroamination of vinylidenecyclopropane-diesters (VDCP-diesters) under mild conditions.
Bibliography:https://doi.org/10.1039/d2cc03635e
Electronic supplementary information (ESI) available: Detailed experimental procedures and analytical data. See DOI
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1359-7345
1364-548X
DOI:10.1039/d2cc03635e