Unprecedented ligand dependent SN2′ mechanism on the palladium-catalyzed nucleophilic substitution to bicyclic dienyl acetates

Hisashi Daimon; Takahiro Kitamura; Tamotsu Kawahara; Isao Shimizu

doi:10.1246/cl.2005.408

Unprecedented ligand dependent S_N2′ mechanism on the palladium-catalyzed nucleophilic substitution to bicyclic dienyl acetates

Hisashi Daimon, Takahiro Kitamura, Tamotsu Kawahara, Isao Shimizu^*

^*Corresponding author for this work

Waseda University

Research output: Contribution to journal › Article › peer-review

4 Citations (Scopus)

Abstract

Palladium-catalyzed nucleophilic reaction to bicyclic dienyl acetates 1 was studied with both optically active substrates and deuterium labeled substrates in order to clarify regioselectivity of the reaction. The regioselectivity depended on phosphine ligands. Thus, S_N2 type reaction was observed using PPh₃. Whereas, unprecedented S_N2′ type reaction proceeded in high yields using DPPP and DPPB, which is applicable to a remote nucleophilic substitution.

Original language	English
Pages (from-to)	408-409
Number of pages	2
Journal	Chemistry Letters
Volume	34
Issue number	3
DOIs	https://doi.org/10.1246/cl.2005.408
Publication status	Published - 2005 Mar 5

ASJC Scopus subject areas

Chemistry(all)

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abstract = "Palladium-catalyzed nucleophilic reaction to bicyclic dienyl acetates 1 was studied with both optically active substrates and deuterium labeled substrates in order to clarify regioselectivity of the reaction. The regioselectivity depended on phosphine ligands. Thus, SN2 type reaction was observed using PPh3. Whereas, unprecedented SN2′ type reaction proceeded in high yields using DPPP and DPPB, which is applicable to a remote nucleophilic substitution.",

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AU - Kitamura, Takahiro

AU - Kawahara, Tamotsu

AU - Shimizu, Isao

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AB - Palladium-catalyzed nucleophilic reaction to bicyclic dienyl acetates 1 was studied with both optically active substrates and deuterium labeled substrates in order to clarify regioselectivity of the reaction. The regioselectivity depended on phosphine ligands. Thus, SN2 type reaction was observed using PPh3. Whereas, unprecedented SN2′ type reaction proceeded in high yields using DPPP and DPPB, which is applicable to a remote nucleophilic substitution.

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Unprecedented ligand dependent S_N2′ mechanism on the palladium-catalyzed nucleophilic substitution to bicyclic dienyl acetates

Abstract

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