A 1,3-carbonyl shift in the platinum-catalyzed aromatization of 2-epoxy-1-(methoxyalk-2-ynyl)benzenes.
نویسندگان
چکیده
A platinum-catalyzed reaction involving new aromatization/1,3-carbonyl shift cascade of 2-epoxy-1-(methoxyalk-2-ynyl)benzenes is reported. This skeletal rearrangement is mechanistically significant because it involves a remarkable 1,3-carbonyl shift to complete the aromatization and to regenerate the catalyst.
منابع مشابه
Highly stereoselective synthesis of (Z)-1,2-dihaloalkenes by a Pd-catalyzed hydrohalogenation of alkynyl halides.
An unprecedented Pd-catalyzed hydrohalogenation of alkynyl halides for the regio- and stereoselective synthesis of (Z)-1,2-dihaloalkenes has been realized using [(allyl)PdCl](2) as the catalyst and cis,cis-1,5-cyclooctadiene as the ligand. The advantages of this protocol are well illustrated by the assembly of trisubstituted (Z)-enynes and multifunctional benzenes via iterative cross-coupling r...
متن کامل1,4-bis(triphenyl phosphonium)butane peroxodisulfate: conversion of alkyl benzenes to carbonyl compounds
1,4-bis(triphenyl phosphonium)butane peroxodisulfate(BTPPBPDS) were synthesized by treating 1,4-bis(triphenyl phosphonium)butane dibromide and potassium peroxydisulfate in aqueous solution.This was used mild and efficient reagent for oxidation of alkyl benzenes to their corresponding carbonyl compounds in very good to high yields.
متن کاملRegio- and stereoselective formation of 1,3-Oxathiolanes by reactions of thiocarbonyl compounds with oxiranes
Lewis acid-catalyzed reactions of oxiranes with a variety of C=S compounds yield 1,3-oxathiolanes. The ring enlargement of monosubstituted oxiranes occurs regioselectively via cleavage of the O,C(3) bond of alkyl substituted oxiranes and the O,C(2) bond of phenyl oxirane. Furthermore, the reaction proceeds with inversion of the configuration at the center of the nucleophilic attack by the S-ato...
متن کاملCarbohydrates to Pyrano-Furanoids: New and Regioselective Palladium-Catalyzed Syntheses of Tetrasubstituted Furanoids from Carbohydrate Scaffolds
Furanoids are important targets either as a key entity itself or as a substructure that represents the framework of many biologically significant natural products [1]. Therefore, their access has attracted the interest of many groups [2], Voelter et al. have described elegant strategies for the syntheses of furanoids using two different approaches, either mono or dianions derived from 1,3-dicar...
متن کاملIridium-Catalyzed 1,3-Hydrogen Shift/Chlorination of Allylic Alcohols**
Chlorinated compounds are among the most common and versatile building blocks in organic synthesis. Among these, achlorocarbonyl derivatives are of synthetic value owing to the variety of functional groups that can be introduced both at the chlorinated a-carbon atom and at the carbonyl functionality. For instance, they readily undergo substitution/addition reactions and cross-coupling reactions...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Chemical communications
دوره 46 25 شماره
صفحات -
تاریخ انتشار 2010