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Regioselective C(sp 2 )−C(sp 3 ) Oxidative Bond Cleavage of 1‐(1‐Hydroxyalkyl) naphthalen‐2‐ols: First Synthesis of 1‐Azido‐halo‐naphthalene‐2(1 H )‐ones
Author(s) -
Kumar Ghosh Manoj,
Roy Barnali,
Sarkar Debayan
Publication year - 2021
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.202000082
Subject(s) - chemistry , bond cleavage , regioselectivity , cleavage (geology) , naphthalene , oxidative cleavage , bromide , oxidative phosphorylation , medicinal chemistry , stereochemistry , organic chemistry , catalysis , biochemistry , geotechnical engineering , fracture (geology) , engineering
A new one‐pot oxidative cleavage of C(sp 2 )−C(sp 3 ) bond has been explored using two complementary protocols employing Phenylselenyl bromide (PhSeBr) as well as Phenyltrimethylammonium Tribromide (PTAB), with much greater efficiency and scope. The oxidative cleavage proceeds via a dearomatization step to afford potentially useful bromonaphthols along with corresponding aldehydes. In this course, we also described the first synthesis of synthetically important azido‐halo naphthaleneones.