A new five-membered ring forming process based on palladium(0)-catalyzed arylative cyclization of allenyl enones

Hirokazu Tsukamoto; Yoshinori Kondo

doi:10.1021/ol800509z

A new five-membered ring forming process based on palladium(0)-catalyzed arylative cyclization of allenyl enones

Hirokazu Tsukamoto, Yoshinori Kondo

PHA - Molecular Pharmaceutical Science

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

18 Citations (Scopus)

Abstract

(Chemical Equation Presented) A palladium(0)/monophosphine catalyst promotes a novel arylative cyclization reaction of C1-, C2-, and C3-tethered allenyl enones with arylboronic acids to produce five-membered ring containing products. The regioselectivity of the process, associated with aryl group introduction into the allene moiety, depends on the length of the tether. This finding suggests that the cyclization reaction does not proceed through a carbopalladation pathway but rather via a route involving palladacycle-forming or "anti-Wacker"-type oxidative addition to the Pd⁰ catalyst.

Original language	English
Pages (from-to)	2633-2636
Number of pages	4
Journal	Organic letters
Volume	10
Issue number	13
DOIs	https://doi.org/10.1021/ol800509z
Publication status	Published - 2008 Dec 1

ASJC Scopus subject areas

Organic Chemistry
Physical and Theoretical Chemistry
Biochemistry
Molecular Medicine

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author = "Hirokazu Tsukamoto and Yoshinori Kondo",

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AU - Kondo, Yoshinori

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Y1 - 2008/12/1

N2 - (Chemical Equation Presented) A palladium(0)/monophosphine catalyst promotes a novel arylative cyclization reaction of C1-, C2-, and C3-tethered allenyl enones with arylboronic acids to produce five-membered ring containing products. The regioselectivity of the process, associated with aryl group introduction into the allene moiety, depends on the length of the tether. This finding suggests that the cyclization reaction does not proceed through a carbopalladation pathway but rather via a route involving palladacycle-forming or "anti-Wacker"-type oxidative addition to the Pd0 catalyst.

AB - (Chemical Equation Presented) A palladium(0)/monophosphine catalyst promotes a novel arylative cyclization reaction of C1-, C2-, and C3-tethered allenyl enones with arylboronic acids to produce five-membered ring containing products. The regioselectivity of the process, associated with aryl group introduction into the allene moiety, depends on the length of the tether. This finding suggests that the cyclization reaction does not proceed through a carbopalladation pathway but rather via a route involving palladacycle-forming or "anti-Wacker"-type oxidative addition to the Pd0 catalyst.

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A new five-membered ring forming process based on palladium(0)-catalyzed arylative cyclization of allenyl enones

Abstract

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