Tags

Type your tag names separated by a space and hit enter

Visible-light-mediated intramolecular radical cyclization of α-brominated amide-tethered alkylidenecyclopropanes.
Chem Commun (Camb). 2022 Mar 15; 58(22):3653-3656.CC

Abstract

A ring-opening/cyclization cascade reaction of α-brominated amide-tethered alkylidenecyclopropanes in the presence of photocatalyst 4CzIPN under visible-light irradiation was developed to afford polycyclic benzazepine derivatives in good yields with broad substrate scope and good functional tolerance. A plausible mechanism involving a halogen atom transfer (XAT) process and a radical chain process is proposed for this reaction. This study provides a concise and practical strategy for the synthesis of benzazepine derivatives.

Links

Publisher Full Text (DOI)

Authors+Show Affiliations

Mao B
Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China.
Zhang XY
Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China.
Wei Y
State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling-Ling Lu, Shanghai, 200032, China. weiyin@sioc.ac.cn.
Shi M
Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China. State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling-Ling Lu, Shanghai, 200032, China. weiyin@sioc.ac.cn.

MeSH

AmidesCyclizationLight

Pub Type(s)

Journal Article

Language

eng

PubMed ID

35213679

Citation

Mao, Ben, et al. "Visible-light-mediated Intramolecular Radical Cyclization of Α-brominated Amide-tethered Alkylidenecyclopropanes." Chemical Communications (Cambridge, England), vol. 58, no. 22, 2022, pp. 3653-3656.
Mao B, Zhang XY, Wei Y, et al. Visible-light-mediated intramolecular radical cyclization of α-brominated amide-tethered alkylidenecyclopropanes. Chem Commun (Camb). 2022;58(22):3653-3656.
Mao, B., Zhang, X. Y., Wei, Y., & Shi, M. (2022). Visible-light-mediated intramolecular radical cyclization of α-brominated amide-tethered alkylidenecyclopropanes. Chemical Communications (Cambridge, England), 58(22), 3653-3656. https://doi.org/10.1039/d1cc07136j
Mao B, et al. Visible-light-mediated Intramolecular Radical Cyclization of Α-brominated Amide-tethered Alkylidenecyclopropanes. Chem Commun (Camb). 2022 Mar 15;58(22):3653-3656. PubMed PMID: 35213679.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Visible-light-mediated intramolecular radical cyclization of α-brominated amide-tethered alkylidenecyclopropanes. AU - Mao,Ben, AU - Zhang,Xiao-Yu, AU - Wei,Yin, AU - Shi,Min, Y1 - 2022/03/15/ PY - 2022/2/26/pubmed PY - 2022/3/18/medline PY - 2022/2/25/entrez SP - 3653 EP - 3656 JF - Chemical communications (Cambridge, England) JO - Chem Commun (Camb) VL - 58 IS - 22 N2 - A ring-opening/cyclization cascade reaction of α-brominated amide-tethered alkylidenecyclopropanes in the presence of photocatalyst 4CzIPN under visible-light irradiation was developed to afford polycyclic benzazepine derivatives in good yields with broad substrate scope and good functional tolerance. A plausible mechanism involving a halogen atom transfer (XAT) process and a radical chain process is proposed for this reaction. This study provides a concise and practical strategy for the synthesis of benzazepine derivatives. SN - 1364-548X UR - https://www.unboundmedicine.com/medline/citation/35213679/Visible_light_mediated_intramolecular_radical_cyclization_of_α_brominated_amide_tethered_alkylidenecyclopropanes_ DB - PRIME DP - Unbound Medicine ER -

Related Citations

More