Remarkable reversal of the regioselectivity in the palladium catalyzed hydrocarbonation reaction of allenes with methylmalononitrile

Yoshinori Yamamoto; Mohammad Al-Masum; Naoya Fujiwara; Naoki Asao

doi:10.1016/0040-4039(95)00403-Y

Remarkable reversal of the regioselectivity in the palladium catalyzed hydrocarbonation reaction of allenes with methylmalononitrile

Yoshinori Yamamoto, Mohammad Al-Masum, Naoya Fujiwara, Naoki Asao

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

56 Citations (Scopus)

Abstract

The palladium catalyzed addition of methylmalononitrile 4a to arylallenes 3 affords the internal adducts 5 and 6 either predominantly or exclusively when an electron-withdrawing group is present at the para-position, whereas it gives the terminal adduct 7 exclusively when an electron-donating group is present at the para-position.

Original language	English
Pages (from-to)	2811-2814
Number of pages	4
Journal	Tetrahedron Letters
Volume	36
Issue number	16
DOIs	https://doi.org/10.1016/0040-4039(95)00403-Y
Publication status	Published - 1995 Apr 17

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Remarkable reversal of the regioselectivity in the palladium catalyzed hydrocarbonation reaction of allenes with methylmalononitrile",

abstract = "The palladium catalyzed addition of methylmalononitrile 4a to arylallenes 3 affords the internal adducts 5 and 6 either predominantly or exclusively when an electron-withdrawing group is present at the para-position, whereas it gives the terminal adduct 7 exclusively when an electron-donating group is present at the para-position.",

author = "Yoshinori Yamamoto and Mohammad Al-Masum and Naoya Fujiwara and Naoki Asao",

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T1 - Remarkable reversal of the regioselectivity in the palladium catalyzed hydrocarbonation reaction of allenes with methylmalononitrile

AU - Yamamoto, Yoshinori

AU - Al-Masum, Mohammad

AU - Fujiwara, Naoya

AU - Asao, Naoki

PY - 1995/4/17

Y1 - 1995/4/17

N2 - The palladium catalyzed addition of methylmalononitrile 4a to arylallenes 3 affords the internal adducts 5 and 6 either predominantly or exclusively when an electron-withdrawing group is present at the para-position, whereas it gives the terminal adduct 7 exclusively when an electron-donating group is present at the para-position.

AB - The palladium catalyzed addition of methylmalononitrile 4a to arylallenes 3 affords the internal adducts 5 and 6 either predominantly or exclusively when an electron-withdrawing group is present at the para-position, whereas it gives the terminal adduct 7 exclusively when an electron-donating group is present at the para-position.

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