Palladium-catalyzed 5-exo-Selective Reductive Mizoroki-Heck Reaction of Aryl Chlorides with 2,5-Norbornadiene

5-exo-Selective reductive Mizoroki-Heck reaction of 4-tert-butyl-l-chlorobenzene with 2,5-norbornadiene has been achieved by [PdCl2(PCy3)(2)]/HCO2Na to give 5-exo-(4-tert-butylphenyl)-2-norbornene in 95% yield. When Cs2CO3 is used as a base in the absence of a reducing reagent, an exo-benzocyclobute...

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Bibliographic Details
Published inChemistry letters Vol. 44; no. 5; pp. 715 - 717
Main Authors Aida, Fuyuki, Sone, Hisashi, Ogawa, Ryuhei, Hamaoka, Takeharu, Shimizu, Isao
Format Journal Article
LanguageEnglish
Published TOKYO Chemical Soc Japan 05.05.2015
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
ALKENES
HETEROCYCLES
PALLADACYCLES
ANNULATION
ARYLATION
COMPLEXES
DERIVATIVES
SELECTIVE HYDROGENOLYSIS
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Summary:5-exo-Selective reductive Mizoroki-Heck reaction of 4-tert-butyl-l-chlorobenzene with 2,5-norbornadiene has been achieved by [PdCl2(PCy3)(2)]/HCO2Na to give 5-exo-(4-tert-butylphenyl)-2-norbornene in 95% yield. When Cs2CO3 is used as a base in the absence of a reducing reagent, an exo-benzocyclobutene-fused norbomene, 6-tert-buty1-1,4,4a,8b-tetrahydro-1,4-methanobiphenylene is produced in 62% yield.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.150099