Inter- and intramolecular palladium-catalyzed hydrocarbonation of methylenecyclopropanes with carbon pronucleophiles

Naofumi Tsukada; Akinori Shibuya; Itaru Nakamura; Haruo Kitahara; Yoshinori Yamamoto

doi:10.1016/S0040-4020(99)00447-0

Inter- and intramolecular palladium-catalyzed hydrocarbonation of methylenecyclopropanes with carbon pronucleophiles

Naofumi Tsukada, Akinori Shibuya, Itaru Nakamura, Haruo Kitahara, Yoshinori Yamamoto

SCI - Research and Analytical Center for Giant Molecules

Tohoku University

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

29 Citations (Scopus)

Abstract

The inter- and intramolecular additions of pronucleophiles to methylenecyclopropanes proceeded smoothly in the presence of catalytic amounts of Pd(PPh₃)₄, affording hydrocarbonation products in good to high yields. The ring opening of methylenecyclopropanes mainly occurred at the distal position to the exomethylene. In some cases, proximal bond cleavage also took place. The mode of ring opening depended upon both the structure of the pronucleophile and the substituent at the exomethylene carbon.

Original language	English
Pages (from-to)	8833-8844
Number of pages	12
Journal	Tetrahedron
Volume	55
Issue number	29
DOIs	https://doi.org/10.1016/S0040-4020(99)00447-0
Publication status	Published - 1999 Jul 16

Keywords

Hydrocarbonation
Methylenecyclopropane
Palladium catalyzed reaction
Pronucleophile

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10.1016/S0040-4020(99)00447-0

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title = "Inter- and intramolecular palladium-catalyzed hydrocarbonation of methylenecyclopropanes with carbon pronucleophiles",

abstract = "The inter- and intramolecular additions of pronucleophiles to methylenecyclopropanes proceeded smoothly in the presence of catalytic amounts of Pd(PPh3)4, affording hydrocarbonation products in good to high yields. The ring opening of methylenecyclopropanes mainly occurred at the distal position to the exomethylene. In some cases, proximal bond cleavage also took place. The mode of ring opening depended upon both the structure of the pronucleophile and the substituent at the exomethylene carbon.",

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author = "Naofumi Tsukada and Akinori Shibuya and Itaru Nakamura and Haruo Kitahara and Yoshinori Yamamoto",

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T1 - Inter- and intramolecular palladium-catalyzed hydrocarbonation of methylenecyclopropanes with carbon pronucleophiles

AU - Tsukada, Naofumi

AU - Shibuya, Akinori

AU - Nakamura, Itaru

AU - Kitahara, Haruo

AU - Yamamoto, Yoshinori

PY - 1999/7/16

Y1 - 1999/7/16

N2 - The inter- and intramolecular additions of pronucleophiles to methylenecyclopropanes proceeded smoothly in the presence of catalytic amounts of Pd(PPh3)4, affording hydrocarbonation products in good to high yields. The ring opening of methylenecyclopropanes mainly occurred at the distal position to the exomethylene. In some cases, proximal bond cleavage also took place. The mode of ring opening depended upon both the structure of the pronucleophile and the substituent at the exomethylene carbon.

AB - The inter- and intramolecular additions of pronucleophiles to methylenecyclopropanes proceeded smoothly in the presence of catalytic amounts of Pd(PPh3)4, affording hydrocarbonation products in good to high yields. The ring opening of methylenecyclopropanes mainly occurred at the distal position to the exomethylene. In some cases, proximal bond cleavage also took place. The mode of ring opening depended upon both the structure of the pronucleophile and the substituent at the exomethylene carbon.

KW - Hydrocarbonation

KW - Methylenecyclopropane

KW - Palladium catalyzed reaction

KW - Pronucleophile

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AN - SCOPUS:0033575494

SN - 0040-4020

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SP - 8833

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JO - Tetrahedron

JF - Tetrahedron

IS - 29

ER -

Inter- and intramolecular palladium-catalyzed hydrocarbonation of methylenecyclopropanes with carbon pronucleophiles

Abstract

Keywords

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