para-Selective C-H amidation of simple arenes with nitriles

Xiang, Shi-Kai; Li, Jin-Mei; Huang, He; Feng, Chun; Ni, Hai-Liang; Chen, Xiao-Zhen; Wang, Bi-Qin; Zhao, Ke-Qing; Hu, Ping; Redshaw, Carl

Abstract

A para-selective C-H amidation of simple arenes with nitriles has been developed. By increasing the amount of arenes, a further meta-selective C-H arylation of the produced amides occurred. Both steric and electronic effects are utilized to control the selectivity, resulting in only para-selective amidation products. The readily available nitriles as amidation reagents instead of amides makes the synthesis of N-arylamides more accessible.

Citation

Xiang, S.-K., Li, J.-M., Huang, H., Feng, C., Ni, H.-L., Chen, X.-Z., Wang, B.-Q., Zhao, K.-Q., Hu, P., & Redshaw, C. (2015). para-Selective C-H amidation of simple arenes with nitriles. Advanced Synthesis and Catalysis, 357(16-17), 3435-3440. https://doi.org/10.1002/adsc.201500651

• Journal Article Type: Article
• Acceptance Date: Jul 7, 2015
• Online Publication Date: Nov 17, 2015
• Publication Date: Nov 16, 2015
• Deposit Date: Mar 18, 2016
• Publicly Available Date: Mar 18, 2016
• Journal: Advanced catalysis and synthesis
• Print ISSN: 1615-4150
• Publisher: Wiley
• Peer Reviewed: Peer Reviewed
• Volume: 357
• Issue: 16-17
• Pages: 3435-3440
• DOI: https://doi.org/10.1002/adsc.201500651
• Keywords: Amidation, Arenes, Copper, Nitriles
• Public URL: https://hull-repository.worktribe.com/output/433819
• Publisher URL: http://onlinelibrary.wiley.com/wol1/doi/10.1002/adsc.201500651/fullhttp://onlinelibrary.wiley.com/doi/10.1002/adsc.201500651/pdf
• Additional Information: This is the peer reviewed version of the following article: Xiang, S.-K., Li, J.-M., Huang, H., Feng, C., Ni, H.-L., Chen, X.-Z., Wang, B.-Q., Zhao, K.-Q., Hu, P. and Redshaw, C. (2015), para-Selective C[BOND]H Amidation of Simple Arenes with Nitriles. Adv. Synth. Catal., 357: 3435–3440. doi:10.1002/adsc.201500651, which has been published in final form at http://onlinelibrary.wiley.com/wol1/doi/10.1002/adsc.201500651/full. This article may be used for non-commercial purposes in accordance With Wiley Terms and Conditions for self-archiving.
• Contract Date: Mar 18, 2016