Transition-Metal-Free One-Pot Synthesis of Naphthoquinonefuran Derivatives Through Sequential Nucleophilic Substitution–Nucleophilic Addition Reaction

Autor:	Jing Zhang, Jinsong Peng, Peng Sun, Chunxia Chen, Dun Zhou, Xiang Li, Kaijun Xie, Aihong Fan
Rok vydání:	2020
Předmět:	Annulation Nucleophilic addition Transition metal Nucleophile Chemistry Intramolecular force Organic Chemistry One-pot synthesis Nucleophilic substitution Regioselectivity Combinatorial chemistry
Zdroj:	The Journal of Organic Chemistry. 85:9313-9320
ISSN:	1520-6904 0022-3263
DOI:	10.1021/acs.joc.0c00513
Popis:	A transition-metal-free route for tandem one-pot synthesis of naphthoquinonefuran derivatives from 2-hydroxynaphthoquinones has been developed. The sequentially accomplished process comprises an intermolecular alkynylation of sp2-carbon at the 3 position of 2-hydroxynaphthoquinones with arylethynyl bromides, followed by a base-promoted intramolecular nucleophilic annulation reaction. A broad range of functional groups is compatible with this reaction, and diverse naphtho[2,3-b]furan-4,9-diones can be obtained with good yields and excellent regioselectivity.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::9511ff63025b5678681d47dfb6740ce9 https://doi.org/10.1021/acs.joc.0c00513 Zobrazit plný text záznamu