Palladium-catalyzed 5-exo-selective reductive Mizoroki-Heck reaction of aryl chlorides with 2,5-norbornadiene

Fuyuki Aida; Hisashi Sone; Ryuhei Ogawa; Takeharu Hamaoka; Isao Shimizu

doi:10.1246/cl.150099

Palladium-catalyzed 5-exo-selective reductive Mizoroki-Heck reaction of aryl chlorides with 2,5-norbornadiene

Fuyuki Aida^*, Hisashi Sone, Ryuhei Ogawa, Takeharu Hamaoka, Isao Shimizu

^*Corresponding author for this work

Waseda University

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

8 Citations (Scopus)

Abstract

5-exo-Selective reductive Mizoroki-Heck reaction of 4-tert-butyl-1-chlorobenzene with 2,5-norbornadiene has been achieved by [PdCl<inf>2</inf>(PCy<inf>3</inf>)<inf>2</inf>]/HCO<inf>2</inf>Na to give 5-exo-(4-tertbutylphenyl)-2-norbornene in 95% yield. When Cs<inf>2</inf>CO<inf>3</inf> is used as a base in the absence of a reducing reagent, an exo-benzocyclobutene-fused norbornene, 6-tert-butyl-1,4,4a,8b-tetrahydro-1,4-methanobiphenylene is produced in 62% yield.

Original language	English
Pages (from-to)	715-717
Number of pages	3
Journal	Chemistry Letters
Volume	44
Issue number	5
DOIs	https://doi.org/10.1246/cl.150099
Publication status	Published - 2015

ASJC Scopus subject areas

Chemistry(all)

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title = "Palladium-catalyzed 5-exo-selective reductive Mizoroki-Heck reaction of aryl chlorides with 2,5-norbornadiene",

abstract = "5-exo-Selective reductive Mizoroki-Heck reaction of 4-tert-butyl-1-chlorobenzene with 2,5-norbornadiene has been achieved by [PdCl2(PCy3)2]/HCO2Na to give 5-exo-(4-tertbutylphenyl)-2-norbornene in 95% yield. When Cs2CO3 is used as a base in the absence of a reducing reagent, an exo-benzocyclobutene-fused norbornene, 6-tert-butyl-1,4,4a,8b-tetrahydro-1,4-methanobiphenylene is produced in 62% yield.",

author = "Fuyuki Aida and Hisashi Sone and Ryuhei Ogawa and Takeharu Hamaoka and Isao Shimizu",

year = "2015",

doi = "10.1246/cl.150099",

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journal = "Chemistry Letters",

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T1 - Palladium-catalyzed 5-exo-selective reductive Mizoroki-Heck reaction of aryl chlorides with 2,5-norbornadiene

AU - Aida, Fuyuki

AU - Sone, Hisashi

AU - Ogawa, Ryuhei

AU - Hamaoka, Takeharu

AU - Shimizu, Isao

PY - 2015

Y1 - 2015

N2 - 5-exo-Selective reductive Mizoroki-Heck reaction of 4-tert-butyl-1-chlorobenzene with 2,5-norbornadiene has been achieved by [PdCl2(PCy3)2]/HCO2Na to give 5-exo-(4-tertbutylphenyl)-2-norbornene in 95% yield. When Cs2CO3 is used as a base in the absence of a reducing reagent, an exo-benzocyclobutene-fused norbornene, 6-tert-butyl-1,4,4a,8b-tetrahydro-1,4-methanobiphenylene is produced in 62% yield.

AB - 5-exo-Selective reductive Mizoroki-Heck reaction of 4-tert-butyl-1-chlorobenzene with 2,5-norbornadiene has been achieved by [PdCl2(PCy3)2]/HCO2Na to give 5-exo-(4-tertbutylphenyl)-2-norbornene in 95% yield. When Cs2CO3 is used as a base in the absence of a reducing reagent, an exo-benzocyclobutene-fused norbornene, 6-tert-butyl-1,4,4a,8b-tetrahydro-1,4-methanobiphenylene is produced in 62% yield.

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Palladium-catalyzed 5-exo-selective reductive Mizoroki-Heck reaction of aryl chlorides with 2,5-norbornadiene

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