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

Research output: Contribution to journalArticle

2 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 languageEnglish
Pages (from-to)715-717
Number of pages3
JournalChemistry Letters
Volume44
Issue number5
DOIs
Publication statusPublished - 2015

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Palladium
Chlorides
2-norbornene
2,5-norbornadiene
chlorobenzene
benzocyclobutene
palladium chloride

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Palladium-catalyzed 5-exo-selective reductive Mizoroki-Heck reaction of aryl chlorides with 2,5-norbornadiene. / Aida, Fuyuki; Sone, Hisashi; Ogawa, Ryuhei; Hamaoka, Takeharu; Shimizu, Isao.

In: Chemistry Letters, Vol. 44, No. 5, 2015, p. 715-717.

Research output: Contribution to journalArticle

Aida, Fuyuki ; Sone, Hisashi ; Ogawa, Ryuhei ; Hamaoka, Takeharu ; Shimizu, Isao. / Palladium-catalyzed 5-exo-selective reductive Mizoroki-Heck reaction of aryl chlorides with 2,5-norbornadiene. In: Chemistry Letters. 2015 ; Vol. 44, No. 5. pp. 715-717.
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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.",
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