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Arene Trifunctionalization with Highly Fused Ring Systems through a Domino Aryne Nucleophilic and Diels-Alder Cascade.

Abstract

A convenient and efficient domino aryne process was developed under transition-metal-free conditions to generate a range of tetra- and pentacyclic ring systems. This transformation was realized via a 1,2-benzdiyne through a nucleophilic and Diels-Alder reaction cascade using styrene as the diene moiety. Three new chemical bonds, namely one C-N and two C-C bonds, and two benzofused rings could be constructed concomitantly, which was made possible by distinct chemoselective control at both the 1,2-aryne and 2,3-aryne stages. Moreover, in-depth studies were carried out on the domino aryne precursors and controlling the diastereoselectivity.

Authors+Show Affiliations

School of Chemistry and Chemical Engineering, Chongqing University, 174 Shazheng St., Chongqing, 400030, P. R. China.School of Chemistry and Chemical Engineering, Chongqing University, 174 Shazheng St., Chongqing, 400030, P. R. China.School of Chemistry and Chemical Engineering, Chongqing University, 174 Shazheng St., Chongqing, 400030, P. R. China.School of Chemistry and Chemical Engineering, Chongqing University, 174 Shazheng St., Chongqing, 400030, P. R. China.School of Chemistry and Chemical Engineering, Chongqing University, 174 Shazheng St., Chongqing, 400030, P. R. China.School of Chemistry and Chemical Engineering, Chongqing University, 174 Shazheng St., Chongqing, 400030, P. R. China.School of Chemistry and Chemical Engineering, Chongqing University, 174 Shazheng St., Chongqing, 400030, P. R. China.School of Chemistry and Chemical Engineering, Chongqing University, 174 Shazheng St., Chongqing, 400030, P. R. China.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

31596040

Citation

He, Jia, et al. "Arene Trifunctionalization With Highly Fused Ring Systems Through a Domino Aryne Nucleophilic and Diels-Alder Cascade." Angewandte Chemie (International Ed. in English), 2019.
He J, Jia Z, Tan H, et al. Arene Trifunctionalization with Highly Fused Ring Systems through a Domino Aryne Nucleophilic and Diels-Alder Cascade. Angew Chem Int Ed Engl. 2019.
He, J., Jia, Z., Tan, H., Luo, X., Qiu, D., Shi, J., ... Li, Y. (2019). Arene Trifunctionalization with Highly Fused Ring Systems through a Domino Aryne Nucleophilic and Diels-Alder Cascade. Angewandte Chemie (International Ed. in English), doi:10.1002/anie.201911730.
He J, et al. Arene Trifunctionalization With Highly Fused Ring Systems Through a Domino Aryne Nucleophilic and Diels-Alder Cascade. Angew Chem Int Ed Engl. 2019 Oct 9; PubMed PMID: 31596040.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Arene Trifunctionalization with Highly Fused Ring Systems through a Domino Aryne Nucleophilic and Diels-Alder Cascade. AU - He,Jia, AU - Jia,Zizi, AU - Tan,Hongcheng, AU - Luo,Xiaohua, AU - Qiu,Dachuan, AU - Shi,Jiarong, AU - Xu,Hai, AU - Li,Yang, Y1 - 2019/10/09/ PY - 2019/09/12/received PY - 2019/10/10/pubmed PY - 2019/10/10/medline PY - 2019/10/10/entrez KW - arenes KW - arynes KW - benzdiynes KW - domino reactions KW - fused ring systems JF - Angewandte Chemie (International ed. in English) JO - Angew. Chem. Int. Ed. Engl. N2 - A convenient and efficient domino aryne process was developed under transition-metal-free conditions to generate a range of tetra- and pentacyclic ring systems. This transformation was realized via a 1,2-benzdiyne through a nucleophilic and Diels-Alder reaction cascade using styrene as the diene moiety. Three new chemical bonds, namely one C-N and two C-C bonds, and two benzofused rings could be constructed concomitantly, which was made possible by distinct chemoselective control at both the 1,2-aryne and 2,3-aryne stages. Moreover, in-depth studies were carried out on the domino aryne precursors and controlling the diastereoselectivity. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/31596040/Arene_Trifunctionalization_with_Highly_Fused_Ring_Systems_through_Domino_Aryne_Nucleophilic,_Diels-Alder_Cascade L2 - https://doi.org/10.1002/anie.201911730 DB - PRIME DP - Unbound Medicine ER -