A palladium-mediated tandem carbon-carbon bond forming method featuring nucleophilic substitution of intermediate π-allylpalladium complexes produced via the heck reaction

Christine S. Nylund; Daniel T. Smith; John M. Klopp; Steven M. Weinreb

doi:10.1016/0040-4020(95)00518-D

A palladium-mediated tandem carbon-carbon bond forming method featuring nucleophilic substitution of intermediate π-allylpalladium complexes produced via the heck reaction

Christine S. Nylund
, Daniel T. Smith
, John M. Klopp
, Steven M. Weinreb

Chemistry

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

16 Scopus citations

Abstract

Carbon nucleophiles are alkylated with π-allylpalladium complexes formed by the palladium-catalyzed Heck reaction of a vinyl bromide and an olefin. This methodology achieves the consecutive formation of two carbon-carbon bonds in one simple operation and can be applied both inter- and intramolecularly. The rapid construction of functionalized carbobicyclic compounds is effected by the intramolecular version of this condensation.

Original language	English (US)
Pages (from-to)	9301-9318
Number of pages	18
Journal	Tetrahedron
Volume	51
Issue number	34
DOIs	https://doi.org/10.1016/0040-4020(95)00518-D
State	Published - Aug 21 1995

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/0040-4020(95)00518-D

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title = "A palladium-mediated tandem carbon-carbon bond forming method featuring nucleophilic substitution of intermediate π-allylpalladium complexes produced via the heck reaction",

abstract = "Carbon nucleophiles are alkylated with π-allylpalladium complexes formed by the palladium-catalyzed Heck reaction of a vinyl bromide and an olefin. This methodology achieves the consecutive formation of two carbon-carbon bonds in one simple operation and can be applied both inter- and intramolecularly. The rapid construction of functionalized carbobicyclic compounds is effected by the intramolecular version of this condensation.",

author = "Nylund, \{Christine S.\} and Smith, \{Daniel T.\} and Klopp, \{John M.\} and Weinreb, \{Steven M.\}",

year = "1995",

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T1 - A palladium-mediated tandem carbon-carbon bond forming method featuring nucleophilic substitution of intermediate π-allylpalladium complexes produced via the heck reaction

AU - Nylund, Christine S.

AU - Smith, Daniel T.

AU - Klopp, John M.

AU - Weinreb, Steven M.

PY - 1995/8/21

Y1 - 1995/8/21

N2 - Carbon nucleophiles are alkylated with π-allylpalladium complexes formed by the palladium-catalyzed Heck reaction of a vinyl bromide and an olefin. This methodology achieves the consecutive formation of two carbon-carbon bonds in one simple operation and can be applied both inter- and intramolecularly. The rapid construction of functionalized carbobicyclic compounds is effected by the intramolecular version of this condensation.

AB - Carbon nucleophiles are alkylated with π-allylpalladium complexes formed by the palladium-catalyzed Heck reaction of a vinyl bromide and an olefin. This methodology achieves the consecutive formation of two carbon-carbon bonds in one simple operation and can be applied both inter- and intramolecularly. The rapid construction of functionalized carbobicyclic compounds is effected by the intramolecular version of this condensation.

UR - https://www.scopus.com/pages/publications/0029123688

UR - https://www.scopus.com/pages/publications/0029123688#tab=citedBy

U2 - 10.1016/0040-4020(95)00518-D

DO - 10.1016/0040-4020(95)00518-D

M3 - Article

AN - SCOPUS:0029123688

SN - 0040-4020

VL - 51

SP - 9301

EP - 9318

JO - Tetrahedron

JF - Tetrahedron

IS - 34

ER -

A palladium-mediated tandem carbon-carbon bond forming method featuring nucleophilic substitution of intermediate π-allylpalladium complexes produced via the heck reaction

Abstract

All Science Journal Classification (ASJC) codes

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