Letter
Convenient Synthesis of Palladium Nanoparticles and Catalysis of Hiyama Coupling Reaction in Water
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Abstract

An efficient synthesis of Pd nanoparticles in water has been developed using a Fischer carbene complex of tungsten as the reductant and PEG as the capping agent. The colloidal palladium (1 mol %) efficiently catalyzes Hiyama cross-coupling reactions performed in air. Excellent yields of products were obtained with a wide range of substrates. Catalytic activity and stability of the nanoparticles were found to be inversely correlated.
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This article has been cited by 8 ACS Journal articles (5 most recent appear below).

Hiyama Cross-Coupling of Arenediazonium Salts under Mild Reaction Conditions
Kai Cheng, Chen Wang, Yiyuan Ding, Qingbao Song, Chenze Qi, and Xian-Man ZhangThe Journal of Organic Chemistry2011 76 (22), 9261-9268Hiyama Cross-Coupling of Arenediazonium Salts under Mild Reaction Conditions
Kai Cheng, Chen Wang, Yiyuan Ding, Qingbao Song, Chenze Qi, and Xian-Man ZhangThe Journal of Organic Chemistry2011 76 (22), 9261-9268Palladium acetate [Pd(OAc)2]-catalyzed Hiyama cross-coupling of arenediazonium salts with organosilanes was found to generate biaryl products in high yields in alcoholic solutions. The simple and efficient protocol does not require any bases, ligands, or ...

Fluoride-Promoted Cross-Coupling of Chloro(mono-, di-, or triphenyl)germanes with Aryl Halides in “Moist” Toluene. Multiple Transfer of the Phenyl Group from Organogermane Substrates and Comparison of the Coupling Efficiencies of Chloro(phenyl)germanes with their Corresponding Stannane and Silane Counterparts
Jean-Philippe Pitteloud, Zun-Ting Zhang, Yong Liang, Laura Cabrera, and Stanislaw F. WnukThe Journal of Organic Chemistry2010 75 (23), 8199-8212Fluoride-Promoted Cross-Coupling of Chloro(mono-, di-, or triphenyl)germanes with Aryl Halides in “Moist” Toluene. Multiple Transfer of the Phenyl Group from Organogermane Substrates and Comparison of the Coupling Efficiencies of Chloro(phenyl)germanes with their Corresponding Stannane and Silane Counterparts
Jean-Philippe Pitteloud, Zun-Ting Zhang, Yong Liang, Laura Cabrera, and Stanislaw F. WnukThe Journal of Organic Chemistry2010 75 (23), 8199-8212The trichlorophenyl-, dichlorodiphenyl-, and chlorotriphenylgermanes undergo Pd-catalyzed cross-couplings with aryl bromides and iodides in the presence of tetrabutylammonium fluoride in toluene with addition of the measured amount of water. One chloride ...

Highly Chemoselective Baylis−Hillman and Aldol Reactions of 2H-Thiopyran-4(3H)-one Using Tertiary Amine Catalysts in Aqueous Media
Bagher Eftekhari-Sis, Ali Akbari, and Klaus HarmsOrganic Letters2010 12 (20),Highly Chemoselective Baylis−Hillman and Aldol Reactions of 2H-Thiopyran-4(3H)-one Using Tertiary Amine Catalysts in Aqueous Media
Bagher Eftekhari-Sis, Ali Akbari, and Klaus HarmsOrganic Letters2010 12 (20),For the first time, the Baylis−Hillman (BH) reaction of 2H-thiopyran-4(3H)-one is investigated, and surprisingly, the reaction of 2H-thiopyran-4(3H)-one with aldehydes in the presence of different tertiary amines shows excellent chemo- and ...

Palladium Nanoparticle Catalyzed Hiyama Coupling Reaction of Benzyl Halides
Dipankar Srimani, Ansuman Bej and Amitabha SarkarThe Journal of Organic Chemistry2010 75 (12), 4296-4299Palladium Nanoparticle Catalyzed Hiyama Coupling Reaction of Benzyl Halides
Dipankar Srimani, Ansuman Bej and Amitabha SarkarThe Journal of Organic Chemistry2010 75 (12), 4296-4299An efficient Hiyama coupling reaction between benzylic halide and aryltrialkoxysilane using Pd nanoparticles has been developed. This procedure accommodates various functional groups to yield a diverse range of diarylmethanes which are ubiquitous units of ...

Practical Aspects of Carbon−Carbon Cross-Coupling Reactions Using Heteroarenes
Vincent F. Slagt, André H. M. de Vries, Johannes G. de Vries and Richard M. KelloggOrganic Process Research & Development2010 14 (1), 30-47Practical Aspects of Carbon−Carbon Cross-Coupling Reactions Using Heteroarenes
Vincent F. Slagt, André H. M. de Vries, Johannes G. de Vries and Richard M. KelloggOrganic Process Research & Development2010 14 (1), 30-47The use of cross-coupling reactions for the preparation of alkylated and arylated heteroaromatic compounds has increased tremendously over the past two decades. This has been driven on the one hand by the increasingly complex structures of new drugs, most ...
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History
- Published In Issue August 30, 2007
- Received June 26, 2007
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