Regioselective C(sp²)−C(sp³) Oxidative Bond Cleavage of 1‐(1‐Hydroxyalkyl) naphthalen‐2‐ols: First Synthesis of 1‐Azido‐halo‐naphthalene‐2(1H)‐ones

Abstract

A new one-pot oxidative cleavage of C(sp 2 )À 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.

BF3·Et2O-assisted synthesis of sulfinylated spiro[5.5]trienones from biaryl ynones

“…With our interest in dearomative spirocyclizations, 12 we set out to access sulfinylated spirocyclization of biaryl ynones. Thus, in order to determine the suitable reaction conditions for the anticipated dearomative sulfinylation, we performed a series of reactions with biaryl ynones and sulfinic acids in the presence of a series of oxidants.…”

Visible Light Promoted Brominative Dearomatization of Biaryl Ynones to Spirocycles

“…Over the past decade, visible light driven photoredox catalysis has gained colossal interest in the exploration of novel transformations employing photocatalyst (PC) to promote the reactions under external oxidant-free or reductant-free conditions . Driven by our prolonged interest in dearomative spiro-cyclization chemistry and newly gained interest in visible light promoted reactions, we explored the possibility of brominative carbannulation of biaryl ynones to form spiro[5.5]-trienones. Herein, we would like to introduce the application of riboflavin tetraacetate (RFTA) as a metal-free PC to facilitate the primary photoinduced events.…”