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Rapid, Operationally Simple, and Metal‐free NBS Mediated One‐pot Synthesis of 1,2‐Naphthoquinone from 2‐Naphthol
Author(s) -
Sim Jaeuk,
Jo Hyeju,
Viji Mayavan,
Choi Minho,
Jung JinAh,
Lee Heesoon,
Jung JaeKyung
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201701312
Subject(s) - chemistry , oxidizing agent , reagent , naphthoquinone , combinatorial chemistry , substrate (aquarium) , metal , 1,4 naphthoquinone , organic chemistry , geology , oceanography
A metal‐free, one‐pot synthesis of 1,2‐naphthoquinone was accomplished from 2‐naphthol by utilizing economically cheap NBS under open air conditions. Initial formation of 1,1‐dibromonaphthalen‐2‐one and subsequent transformation afforded the 1,2‐naphthoquinone. This oxidation was completed within 30 min and had broad substrate scope. Moreover, this system tolerated heterocyclic systems and was also applicable to 1,3‐dicarbonyl systems. This practical approach with short reaction times, a simple workup, and insensitivity to moisture could override the usage of expensive and hazardous oxidizing and metal reagents.