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An Efficient Reusable Mesoporous Solid-Based Pd Catalyst for Selective C2 Arylation of Indoles in Water
Duan, Linlin; Fu, Rao; Zhang, Bingsen; Shi, Wen; Chen, Shangjun; Wan, Ying; bszhang@imr.ac.cn; ywan@shnu.edu.cn
2016
Source PublicationACS CATALYSIS
ISSN2155-5435
Volume6Issue:2Pages:1062-1074
AbstractThe completely C2-selective arylation of N-methylindole was achieved by using a reusable solid Pd catalyst and water as a solvent without any other ligands or additives or exclusion of air. The catalysts possess well-dispersed Pd nanoparticles (similar to 1.5 nm), N-containing functional groups (similar to 11 wt %), and uniform mesopores (similar to 5 nm). The turnover frequency (TOF) is calculated to be 82 h(-1). Arylations of both N-H indoles and N-protected indoles with diaryliodonium salts were achieved to give the desired products in high to excellent isolated yields in water. Mercapto-functionalized silica as a selective trapping agent, together with hot filtration, confirms the undetected leaching of Pd. The catalyst samples can be reused at least eight times without any additional activation treatment. The catalytic performance of the Pd catalyst is also compared with the performance of other mesoporous Pd catalysts on silica, carbon, and resins. The catalytic activity and stability of the present catalyst may be related to the well dispersed Pd nanoparticles, the electron-rich environment stabilized by the N-containing functional groups, and the large, uniform mesopores.
description.department[duan, linlin ; fu, rao ; chen, shangjun ; wan, ying] shanghai normal univ, minist educ, key lab resource chem, shanghai key lab rare earth funct mat, shanghai 200234, peoples r china ; [duan, linlin ; fu, rao ; chen, shangjun ; wan, ying] shanghai normal univ, dept chem, shanghai 200234, peoples r china ; [zhang, bingsen ; shi, wen] chinese acad sci, inst met res, shenyang natl lab mat sci, shenyang 110016, peoples r china
KeywordC2 Arylation Pd Cluster Hybrid Mesoporous Polymer Water-mediated Reusability
Funding OrganizationState Key Basic Research Program of China [2013CB934102]; NSF of China [21322308, 21173149]; Ministry of Education of China [PCSIRT-IRT1269, 20123127110004]; International Joint Laboratory on Resource Chemistry (IJLRC); Shanghai Sci. & Tech. and Edu. Committee [11JC1409200, 14YF1409200, DZL123, S30406]; Youth Innovation Promotion Association CAS [2015152]; [NSFC91545119]
Indexed Bysci
Language英语
Document Type期刊论文
Identifierhttp://ir.imr.ac.cn/handle/321006/74624
Collection中国科学院金属研究所
Corresponding Authorbszhang@imr.ac.cn; ywan@shnu.edu.cn
Recommended Citation
GB/T 7714
Duan, Linlin,Fu, Rao,Zhang, Bingsen,et al. An Efficient Reusable Mesoporous Solid-Based Pd Catalyst for Selective C2 Arylation of Indoles in Water[J]. ACS CATALYSIS,2016,6(2):1062-1074.
APA Duan, Linlin.,Fu, Rao.,Zhang, Bingsen.,Shi, Wen.,Chen, Shangjun.,...&ywan@shnu.edu.cn.(2016).An Efficient Reusable Mesoporous Solid-Based Pd Catalyst for Selective C2 Arylation of Indoles in Water.ACS CATALYSIS,6(2),1062-1074.
MLA Duan, Linlin,et al."An Efficient Reusable Mesoporous Solid-Based Pd Catalyst for Selective C2 Arylation of Indoles in Water".ACS CATALYSIS 6.2(2016):1062-1074.
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