Tags

Type your tag names separated by a space and hit enter

Tandem Photoredox Catalysis: Enabling Carbonylative Amidation of Aryl and Alkylhalides.
Angew Chem Int Ed Engl. 2020 Jul 04 [Online ahead of print]AC

Abstract

We report a new visible light-mediated carbonylative amidation of aryl, heteroaryl and alkyl halides. A tandem catalytic cycle of [Ir(ppy) 2 (dtb-bpy)] + generates a potent iridium photoreductant via a second catalytic cycle in the presence of DIPEA which productively engages aryl bromides, iodides and even chlorides as well as primary, secondary and tertiary alkyl iodides. The versatility of the in-situ generated catalyst is illustrated by compatibility with aliphatic and aromatic amines, high functional group tolerance and the late-stage amidation of complex natural products.

Authors+Show Affiliations

University of Melbourne, School of Chemistry, School of Chemistry, Parkville, 3010, Melbourne, AUSTRALIA.University of Melbourne, Chemistry, AUSTRALIA.University of Melbourne, Chemistry, AUSTRALIA.RMIT University School of Applied Sciences, Applied Chemistry, AUSTRALIA.Commonwealth Scientific and Industrial Research Organisation, Manufcaturing, AUSTRALIA.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

32621297

Citation

Polyzos, Anastasios, et al. "Tandem Photoredox Catalysis: Enabling Carbonylative Amidation of Aryl and Alkylhalides." Angewandte Chemie (International Ed. in English), 2020.
Polyzos A, Forni JA, Micic N, et al. Tandem Photoredox Catalysis: Enabling Carbonylative Amidation of Aryl and Alkylhalides. Angew Chem Int Ed Engl. 2020.
Polyzos, A., Forni, J. A., Micic, N., Connell, T. U., & Weragoda, G. (2020). Tandem Photoredox Catalysis: Enabling Carbonylative Amidation of Aryl and Alkylhalides. Angewandte Chemie (International Ed. in English). https://doi.org/10.1002/anie.202006720
Polyzos A, et al. Tandem Photoredox Catalysis: Enabling Carbonylative Amidation of Aryl and Alkylhalides. Angew Chem Int Ed Engl. 2020 Jul 4; PubMed PMID: 32621297.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Tandem Photoredox Catalysis: Enabling Carbonylative Amidation of Aryl and Alkylhalides. AU - Polyzos,Anastasios, AU - Forni,José A, AU - Micic,Nenad, AU - Connell,Timothy U, AU - Weragoda,Geethika, Y1 - 2020/07/04/ PY - 2020/05/08/received PY - 2020/07/01/accepted PY - 2020/07/01/revised PY - 2020/7/5/entrez KW - Flow Chemistry KW - amides KW - carbonylation KW - multicomponent KW - photoredox JF - Angewandte Chemie (International ed. in English) JO - Angew. Chem. Int. Ed. Engl. N2 - We report a new visible light-mediated carbonylative amidation of aryl, heteroaryl and alkyl halides. A tandem catalytic cycle of [Ir(ppy) 2 (dtb-bpy)] + generates a potent iridium photoreductant via a second catalytic cycle in the presence of DIPEA which productively engages aryl bromides, iodides and even chlorides as well as primary, secondary and tertiary alkyl iodides. The versatility of the in-situ generated catalyst is illustrated by compatibility with aliphatic and aromatic amines, high functional group tolerance and the late-stage amidation of complex natural products. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/32621297/Tandem_Photoredox_Catalysis:_Enabling_Carbonylative_Amidation_of_Aryl_and_Alkylhalides L2 - https://doi.org/10.1002/anie.202006720 DB - PRIME DP - Unbound Medicine ER -
Try the Free App:
Prime PubMed app for iOS iPhone iPad
Prime PubMed app for Android
Prime PubMed is provided
free to individuals by:
Unbound Medicine.