Synthesis of Carbobicyclic Compounds via Palladium−Catalyzed Cyclization/Hydrosilylation:  Evidence for Reversible Silylpalladation

Cyclization/hydrosilylation of substituted 1-vinyl-1-(3-butenyl)cycloalkanes catalyzed by a 1:1 mixture of (phen)Pd(Me)Cl (1) and NaBAr4 [phen = 1,10-phenanthroline; Ar = 3,5-C6H3(CF3)2] formed silylated spirocycles in high yield with excellent regio and diastereoselectivity. Cyclization/hydrosilyla...

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Published in:Journal of organic chemistry 2001-03, Vol.66 (5), p.1755-1760
Main Authors: Wang, Xiang, Chakrapani, Harinath, Stengone, Carmine N., Widenhoefer, Ross A.
Format: Article
Language:English
Subjects:
Bridged Bicyclo Compounds, Heterocyclic - chemical synthesis
Bridged Bicyclo Compounds, Heterocyclic - chemistry
Catalysis
Magnetic Resonance Spectroscopy
Molecular Structure
N-Acetylneuraminic Acid - chemistry
Palladium - chemistry
Spectrophotometry, Infrared
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cited_by cdi_FETCH-LOGICAL-a415t-b41b935925912da0d28dfd2b7ebe98c3f65ee84f6a81907e031a0fbe2f61eacc3
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container_end_page 1760
container_issue 5
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container_title Journal of organic chemistry
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creator Wang, Xiang
Chakrapani, Harinath
Stengone, Carmine N.
Widenhoefer, Ross A.
description Cyclization/hydrosilylation of substituted 1-vinyl-1-(3-butenyl)cycloalkanes catalyzed by a 1:1 mixture of (phen)Pd(Me)Cl (1) and NaBAr4 [phen = 1,10-phenanthroline; Ar = 3,5-C6H3(CF3)2] formed silylated spirocycles in high yield with excellent regio and diastereoselectivity. Cyclization/hydrosilylation of substituted 3-(3-butenyl)cycloalkenes or 2,3-diallyl-5,6-dimethyl-1,4-hydroquinone diacetate (16) formed silylated fused bicyclic complexes in good yield. Reaction of substituted 1,6,11-nonatrienes with silane catalyzed by 1/NaBAr4 led to cascade cyclization with hydrosilylation. This latter procedure was employed in the synthesis of silylated bicyclopentanes and a linear triquinane.
doi_str_mv 10.1021/jo001438k
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source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
subjects Bridged Bicyclo Compounds, Heterocyclic - chemical synthesis
Bridged Bicyclo Compounds, Heterocyclic - chemistry
Catalysis
Magnetic Resonance Spectroscopy
Molecular Structure
N-Acetylneuraminic Acid - chemistry
Palladium - chemistry
Spectrophotometry, Infrared
title Synthesis of Carbobicyclic Compounds via Palladium−Catalyzed Cyclization/Hydrosilylation:  Evidence for Reversible Silylpalladation
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