Palladium-catalyzed sequential carbon-carbon bond cleavage/formation producing arylated benzolactones

Takanori Matsuda; Masanori Shigeno; Masahiro Murakami

doi:10.1021/ol802218a

Palladium-catalyzed sequential carbon-carbon bond cleavage/formation producing arylated benzolactones

Takanori Matsuda, Masanori Shigeno, Masahiro Murakami

PHA - Molecular Pharmaceutical Science

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

62 Citations (Scopus)

Abstract

(Chemical Equation Presented) 3-(2-Hydroxyphenyl)cyclobutanones react with aryl bromides in the presence of palladium catalysts to afford 4-arylmethyl-3,4-dihydrocoumarins in high yields through a sequence involving carbon-carbon bond cleavage and formation. In the case of the reaction with 2-(2-hydroxyphenyl)cyclobutanones, five- or seven-membered lactones were produced depending on the presence of an additional substituent at the 2-position.

Original language	English
Pages (from-to)	5219-5221
Number of pages	3
Journal	Organic Letters
Volume	10
Issue number	22
DOIs	https://doi.org/10.1021/ol802218a
Publication status	Published - 2008

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10.1021/ol802218a

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abstract = "(Chemical Equation Presented) 3-(2-Hydroxyphenyl)cyclobutanones react with aryl bromides in the presence of palladium catalysts to afford 4-arylmethyl-3,4-dihydrocoumarins in high yields through a sequence involving carbon-carbon bond cleavage and formation. In the case of the reaction with 2-(2-hydroxyphenyl)cyclobutanones, five- or seven-membered lactones were produced depending on the presence of an additional substituent at the 2-position.",

author = "Takanori Matsuda and Masanori Shigeno and Masahiro Murakami",

year = "2008",

doi = "10.1021/ol802218a",

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journal = "Organic Letters",

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T1 - Palladium-catalyzed sequential carbon-carbon bond cleavage/formation producing arylated benzolactones

AU - Matsuda, Takanori

AU - Shigeno, Masanori

AU - Murakami, Masahiro

PY - 2008

Y1 - 2008

N2 - (Chemical Equation Presented) 3-(2-Hydroxyphenyl)cyclobutanones react with aryl bromides in the presence of palladium catalysts to afford 4-arylmethyl-3,4-dihydrocoumarins in high yields through a sequence involving carbon-carbon bond cleavage and formation. In the case of the reaction with 2-(2-hydroxyphenyl)cyclobutanones, five- or seven-membered lactones were produced depending on the presence of an additional substituent at the 2-position.

AB - (Chemical Equation Presented) 3-(2-Hydroxyphenyl)cyclobutanones react with aryl bromides in the presence of palladium catalysts to afford 4-arylmethyl-3,4-dihydrocoumarins in high yields through a sequence involving carbon-carbon bond cleavage and formation. In the case of the reaction with 2-(2-hydroxyphenyl)cyclobutanones, five- or seven-membered lactones were produced depending on the presence of an additional substituent at the 2-position.

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U2 - 10.1021/ol802218a

DO - 10.1021/ol802218a

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SP - 5219

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JO - Organic Letters

JF - Organic Letters

IS - 22

ER -

Palladium-catalyzed sequential carbon-carbon bond cleavage/formation producing arylated benzolactones

Abstract

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