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Title: Pd-Metalated Conjugated Nanoporous Polycarbazoles for Additive-Free Cyanation of Aryl Halides: Boosting Catalytic Efficiency through Spatial Modulation

Abstract

Transition-metal-catalyzed cyanation of aryl halides is a common route to benzonitriles, which are integral to many industrial procedures. However, traditional homogeneous catalysts for such processes are expensive and suffer poor recyclability, so a heterogeneous analogue is highly desired. A novel spatial modulation approach has been developed in this paper to fabricate a heterogeneous Pd-metalated nanoporous polymer, which catalyzes the cyanation of aryl halides without need for ligands. Finally, the catalyst displays high activity in the synthesis of benzonitriles, including high product yields, excellent stability and recycling, and broad functional-group tolerance.

Authors:
 [1];  [2];  [2]; ORCiD logo [3];  [4];  [5];  [2];  [4];  [5]; ORCiD logo [6]
  1. Nanchang Univ. (China). Inst. of Applied Chemistry. College of Chemistry; Univ. of Tennessee, Knoxville, TN (United States). Dept. of Chemistry
  2. Univ. of Tennessee, Knoxville, TN (United States). Dept. of Chemistry
  3. Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Chemical Sciences Division
  4. Univ. of California, Riverside, CA (United States). Dept. of Chemistry
  5. Nanchang Univ. (China). Inst. of Applied Chemistry. College of Chemistry
  6. Univ. of Tennessee, Knoxville, TN (United States). Dept. of Chemistry; Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Chemical Sciences Division
Publication Date:
Research Org.:
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States); Univ. of Tennessee, Knoxville, TN (United States); Nanchang Univ. (China)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22); National Natural Science Foundation of China (NNSFC); Natural Science Foundation of Jiangxi Province (China)
Contributing Org.:
Univ. of California, Riverside, CA (United States)
OSTI Identifier:
1376431
Alternate Identifier(s):
OSTI ID: 1399441
Grant/Contract Number:  
AC05-00OR22725; 21062013; 2011ZBAB203013
Resource Type:
Accepted Manuscript
Journal Name:
ChemSusChem
Additional Journal Information:
Journal Volume: 10; Journal Issue: 11; Journal ID: ISSN 1864-5631
Publisher:
ChemPubSoc Europe
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; cyanation; heterogeneous catalysis; palladium; polymers; porous materials

Citation Formats

Ding, Shunmin, Tian, Chengcheng, Zhu, Xiang, Abney, Carter W., Tian, Ziqi, Chen, Bo, Li, Meijun, Jiang, De-en, Zhang, Ning, and Dai, Sheng. Pd-Metalated Conjugated Nanoporous Polycarbazoles for Additive-Free Cyanation of Aryl Halides: Boosting Catalytic Efficiency through Spatial Modulation. United States: N. p., 2017. Web. doi:10.1002/cssc.201700329.
Ding, Shunmin, Tian, Chengcheng, Zhu, Xiang, Abney, Carter W., Tian, Ziqi, Chen, Bo, Li, Meijun, Jiang, De-en, Zhang, Ning, & Dai, Sheng. Pd-Metalated Conjugated Nanoporous Polycarbazoles for Additive-Free Cyanation of Aryl Halides: Boosting Catalytic Efficiency through Spatial Modulation. United States. doi:10.1002/cssc.201700329.
Ding, Shunmin, Tian, Chengcheng, Zhu, Xiang, Abney, Carter W., Tian, Ziqi, Chen, Bo, Li, Meijun, Jiang, De-en, Zhang, Ning, and Dai, Sheng. Thu . "Pd-Metalated Conjugated Nanoporous Polycarbazoles for Additive-Free Cyanation of Aryl Halides: Boosting Catalytic Efficiency through Spatial Modulation". United States. doi:10.1002/cssc.201700329. https://www.osti.gov/servlets/purl/1376431.
@article{osti_1376431,
title = {Pd-Metalated Conjugated Nanoporous Polycarbazoles for Additive-Free Cyanation of Aryl Halides: Boosting Catalytic Efficiency through Spatial Modulation},
author = {Ding, Shunmin and Tian, Chengcheng and Zhu, Xiang and Abney, Carter W. and Tian, Ziqi and Chen, Bo and Li, Meijun and Jiang, De-en and Zhang, Ning and Dai, Sheng},
abstractNote = {Transition-metal-catalyzed cyanation of aryl halides is a common route to benzonitriles, which are integral to many industrial procedures. However, traditional homogeneous catalysts for such processes are expensive and suffer poor recyclability, so a heterogeneous analogue is highly desired. A novel spatial modulation approach has been developed in this paper to fabricate a heterogeneous Pd-metalated nanoporous polymer, which catalyzes the cyanation of aryl halides without need for ligands. Finally, the catalyst displays high activity in the synthesis of benzonitriles, including high product yields, excellent stability and recycling, and broad functional-group tolerance.},
doi = {10.1002/cssc.201700329},
journal = {ChemSusChem},
number = 11,
volume = 10,
place = {United States},
year = {2017},
month = {3}
}

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