Bridged imidazolium salts used as precursors for chelating carbene complexes of palladium in the Mizoroki-Heck reaction

Tobias Scherg; Sabine K. Schneider; Guido D. Frey; Jürgen Schwarz; Eberhardt Herdtweck; Wolfgang A. Herrmann

doi:10.1055/s-2006-951539

Bridged imidazolium salts used as precursors for chelating carbene complexes of palladium in the Mizoroki-Heck reaction

Tobias Scherg
, Sabine K. Schneider
, Guido D. Frey
, Jürgen Schwarz
, Eberhardt Herdtweck
, Wolfgang A. Herrmann

Technical University of Munich

Technical University of Munich

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

85 Scopus citations

Abstract

A variety of chiral and achiral imidazolium salts is synthesized. Methylene-, ethylene-, propylene- and pyridinyl-bridged bis(imidazolium) halides are used to generate the respective free chelating carbenes. The synthesis of palladium complexes of general formula [cis-CH₂{NC(H)=C(H)N(R)C} ₂PdX₂] with these chelating N-heterocyclic carbene ligands is reported. Structural proofs of complexes 28 and 46 are represented by X-ray diffraction studies. Catalytic applications in the Mizoroki-Heck reaction are presented.

Original language	English
Pages (from-to)	2894-2907
Number of pages	14
Journal	Synlett
Issue number	18
DOIs	https://doi.org/10.1055/s-2006-951539
State	Published - 3 Nov 2006

Keywords

Catalysis
Chelating ligands
Chiral ligands
Free carbenes
Imidazolium salts
Mizoroki-Heck reaction
Palladium

Access to Document

10.1055/s-2006-951539

Cite this

@article{ab2ef73c9d904124b168c588086da1c2,

title = "Bridged imidazolium salts used as precursors for chelating carbene complexes of palladium in the Mizoroki-Heck reaction",

abstract = "A variety of chiral and achiral imidazolium salts is synthesized. Methylene-, ethylene-, propylene- and pyridinyl-bridged bis(imidazolium) halides are used to generate the respective free chelating carbenes. The synthesis of palladium complexes of general formula [cis-CH2\{NC(H)=C(H)N(R)C\} 2PdX2] with these chelating N-heterocyclic carbene ligands is reported. Structural proofs of complexes 28 and 46 are represented by X-ray diffraction studies. Catalytic applications in the Mizoroki-Heck reaction are presented.",

keywords = "Catalysis, Chelating ligands, Chiral ligands, Free carbenes, Imidazolium salts, Mizoroki-Heck reaction, Palladium",

author = "Tobias Scherg and Schneider, \{Sabine K.\} and Frey, \{Guido D.\} and J{\"u}rgen Schwarz and Eberhardt Herdtweck and Herrmann, \{Wolfgang A.\}",

year = "2006",

month = nov,

day = "3",

doi = "10.1055/s-2006-951539",

language = "English",

pages = "2894--2907",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "18",

}

TY - JOUR

T1 - Bridged imidazolium salts used as precursors for chelating carbene complexes of palladium in the Mizoroki-Heck reaction

AU - Scherg, Tobias

AU - Schneider, Sabine K.

AU - Frey, Guido D.

AU - Schwarz, Jürgen

AU - Herdtweck, Eberhardt

AU - Herrmann, Wolfgang A.

PY - 2006/11/3

Y1 - 2006/11/3

N2 - A variety of chiral and achiral imidazolium salts is synthesized. Methylene-, ethylene-, propylene- and pyridinyl-bridged bis(imidazolium) halides are used to generate the respective free chelating carbenes. The synthesis of palladium complexes of general formula [cis-CH2{NC(H)=C(H)N(R)C} 2PdX2] with these chelating N-heterocyclic carbene ligands is reported. Structural proofs of complexes 28 and 46 are represented by X-ray diffraction studies. Catalytic applications in the Mizoroki-Heck reaction are presented.

AB - A variety of chiral and achiral imidazolium salts is synthesized. Methylene-, ethylene-, propylene- and pyridinyl-bridged bis(imidazolium) halides are used to generate the respective free chelating carbenes. The synthesis of palladium complexes of general formula [cis-CH2{NC(H)=C(H)N(R)C} 2PdX2] with these chelating N-heterocyclic carbene ligands is reported. Structural proofs of complexes 28 and 46 are represented by X-ray diffraction studies. Catalytic applications in the Mizoroki-Heck reaction are presented.

KW - Catalysis

KW - Chelating ligands

KW - Chiral ligands

KW - Free carbenes

KW - Imidazolium salts

KW - Mizoroki-Heck reaction

KW - Palladium

UR - https://www.scopus.com/pages/publications/33751279966

U2 - 10.1055/s-2006-951539

DO - 10.1055/s-2006-951539

M3 - Article

AN - SCOPUS:33751279966

SN - 0936-5214

SP - 2894

EP - 2907

JO - Synlett

JF - Synlett

IS - 18

ER -

Bridged imidazolium salts used as precursors for chelating carbene complexes of palladium in the Mizoroki-Heck reaction

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this