QIBEBT-IR
Additive-modulated switchable reaction pathway in the addition of alkynes with organosilanes catalyzed by supported Pd nanoparticles: hydrosilylation versus semihydrogenation
Duan, Yanan; Ji, Guijie; Zhang, Shaochun; Chen, Xiufang; Yang, Yong
2018-02-21
Source PublicationCATALYSIS SCIENCE & TECHNOLOGY
ISSN2044-4753
Volume8Issue:4Pages:1039-1050
AbstractWe herein report supported Pd nanoparticles on N,O-doped hierarchical porous carbon as a single operation catalyst-enabled additive-modulated reaction pathway for alkynes addition with organosilanes between hydrosilyation and semihydrogenation. In the case of alkynes hydrosilylation, a simple iodide ion as an additive has a promotion effect on the activity and regio- and stereoselectivity, where iodide can coordinate with Pd NPs via strong delta donation to increase the electron density of the Pd atom, resulting in an increased ability for the oxidative addition of hydrosilane as the rate-determining step to make the reaction proceed efficiently to afford vinylsilanes in high yields with excellent regio-and stereoselectivity. For the catalytic transfer semihydrogenation of alkynes, water was introduced to mix with organosilane to form a silanol together with the generation of hydrogen atoms on the Pd NPs surface or the liberation of H-2 gas as a reducing agent, whereby the quantitative reduction of alkynes was achieved with exclusive selectivity to alkenes. In both cases, the catalyst could be recycled several times without a significant loss in activity or selectivity. A broad range of alkyl and aryl alkynes with various functional groups are compatible with the reaction conditions. The role the additive exerted in each reaction was extensively investigated through control experiments as well as the kinetic isotopic effect along with spectroscopic characterization. In addition, the respective mechanism operating in both reactions was proposed.
SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences
DOI10.1039/c7cy02280h
WOS KeywordHIGHLY SELECTIVE SEMIHYDROGENATION ; CARBENE PLATINUM(0) COMPLEXES ; N-HETEROCYCLIC CARBENES ; CARBON MULTIPLE BONDS ; 8 METAL COMPLEXES ; STEREOSELECTIVE HYDROSILYLATION ; TERMINAL ALKYNES ; INTERNAL ALKYNES ; RUTHENIUM COMPLEXES ; CIS-ALKENES
Indexed BySCI
Language英语
WOS Research AreaChemistry
Funding OrganizationQingdao Institute of Bioenergy and Bioprocess Technology (QIBEBT) ; Chinese Academy of Sciences(Y6710619KL) ; 13th-Five Key Project of the Chinese Academy of Sciences(Y7720519KL)
WOS SubjectChemistry, Physical
WOS IDWOS:000427152800011
PublisherROYAL SOC CHEMISTRY
Citation statistics
Document Type期刊论文
Identifierhttp://ir.qibebt.ac.cn/handle/337004/10682
Collection中国科学院青岛生物能源与过程研究所
Corresponding AuthorZhang, Shaochun; Yang, Yong
AffiliationChinese Acad Sci, Qingdao Inst Bioenergy & Bioproc Technol, CAS Key Lab Biobased Mat, Qingdao 266101, Peoples R China
Recommended Citation
GB/T 7714
Duan, Yanan,Ji, Guijie,Zhang, Shaochun,et al. Additive-modulated switchable reaction pathway in the addition of alkynes with organosilanes catalyzed by supported Pd nanoparticles: hydrosilylation versus semihydrogenation[J]. CATALYSIS SCIENCE & TECHNOLOGY,2018,8(4):1039-1050.
APA Duan, Yanan,Ji, Guijie,Zhang, Shaochun,Chen, Xiufang,&Yang, Yong.(2018).Additive-modulated switchable reaction pathway in the addition of alkynes with organosilanes catalyzed by supported Pd nanoparticles: hydrosilylation versus semihydrogenation.CATALYSIS SCIENCE & TECHNOLOGY,8(4),1039-1050.
MLA Duan, Yanan,et al."Additive-modulated switchable reaction pathway in the addition of alkynes with organosilanes catalyzed by supported Pd nanoparticles: hydrosilylation versus semihydrogenation".CATALYSIS SCIENCE & TECHNOLOGY 8.4(2018):1039-1050.
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