2005
DOI: 10.1002/ejoc.200500319
|View full text |Cite
|
Sign up to set email alerts
|

Abstract: The (dipyridin‐2‐ylmethyl)amine‐derived palladium chloride complex 1 and PdCl2 are efficient catalysts for cross‐coupling reactions between terminal alkynes and aryl iodides or bromides under modified Sonogashira–Cassar–Heck conditions. The alkynylation can be performed under copper‐free conditions in water at reflux or at room temperature under air with pyrrolidine as base and tetra‐n‐butylammonium bromide (TBAB) as additive, with TONs of up to 7 × 104 and TOFs(h–1) of up to 6666. Terminal alkynes can be aryl… Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
2
1
1

Citation Types

0
38
0
3

Year Published

2006
2006
2013
2013

Publication Types

Select...
5
4

Relationship

2
7

Authors

Journals

citations
Cited by 103 publications
(41 citation statements)
references
References 69 publications
(24 reference statements)
0
38
0
3
Order By: Relevance
“…It has been shown that the coupling of aryl iodides or bromides with terminal alkynes proceeded smoothly in the presence of pyrrolidine and tetrabutylammonium acetate (TBAB) at 100 8C in water. [62,63] However, the reactions were shown to be faster in NMP solvent than in water under the reaction conditions. Palladium-phosphinous acid (POPd) was also reported as an effective catalyst for Sonogashira crosscoupling reaction of aryl alkynes with aryl iodides, bromides or chlorides in water [Eq.…”
Section: Introductionmentioning
confidence: 96%
“…It has been shown that the coupling of aryl iodides or bromides with terminal alkynes proceeded smoothly in the presence of pyrrolidine and tetrabutylammonium acetate (TBAB) at 100 8C in water. [62,63] However, the reactions were shown to be faster in NMP solvent than in water under the reaction conditions. Palladium-phosphinous acid (POPd) was also reported as an effective catalyst for Sonogashira crosscoupling reaction of aryl alkynes with aryl iodides, bromides or chlorides in water [Eq.…”
Section: Introductionmentioning
confidence: 96%
“…The use of the bis(2-pyridyl)methylamine-palladium dichloride complex, which is eventually anchored covalently to a styrene-maleic anhydride copolymer, is described by Nájera and co-workers for microwave-assisted Heck, Suzuki and Sonogashira cross-coupling reactions in water resulting in high TONs (Scheme 30). [43] Scheme 30. Bis(2-pyridyl)methylamine-palladium dichloride complexes for C-C cross-coupling reactions in water.…”
Section: Microwave-assisted Heck and Sonogashira Reactionsmentioning
confidence: 99%
“…[94] Die elektronenreichen, sperrigen und wasserlöslichen Alkylmonophosphane 4 [95] und 5 [33] [33] Die ionischen Guanidin-Phosphane 6 und 7 vermittelten die Kupplung von wasserlöslichen Iodarenen mit terminalen Alkinen unter biologischen Bedingungen. [96] [50,51] Die kupferfreien Reaktionen wurden in siedendem Wasser mit 0.5-0.01 Mol-% 8, 50-100 Mol-% Tetra-n-butylammoniumbromid (TBAB) und 2 ¾quivalenten Pyrrolidin als Base ausgeführt. Obwohl oft geringe Mengen (5-20 %) Nebenprodukte durch Homokupplung von Acetylenen entstanden, erreichten diese Reaktionen gute TONs (Tabelle 6).…”
Section: Katalyse In Wasserhaltiger Lösungunclassified
“…Obwohl oft geringe Mengen (5-20 %) Nebenprodukte durch Homokupplung von Acetylenen entstanden, erreichten diese Reaktionen gute TONs (Tabelle 6). [51] Unter analogen Bedingungen wurde der Palladiumkomplex 9 einer phosphinigen Säure zusammen mit CuI verwendet, um verschiedene Arylhalogenide, einschließlich aktivierter Heteroarylchloride (Pyridinderivate), zu kuppeln. [36] Tabelle 7 fasst die Alkinprodukte und die Reaktionsbedingungen zusammen.…”
Section: Katalyse In Wasserhaltiger Lösungunclassified