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One-Pot Synthesis of meta-Substituted Phenols via Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling and Oxidation

One-Pot Synthesis of meta-Substituted Phenols via Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling and Oxidation

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Title: One-Pot Synthesis of meta-Substituted Phenols via Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling and Oxidation
Author: Wang, Zi
Abstract: We have developed a two-step synthesis of meta-substituted phenols in one pot, in good to excellent yield. A Pd2+ source is the catalyst for both steps of the synthesis, which includes a cross-coupling reaction between -chlorocyclohexenones with boronic acids, followed by aerobic oxidation of the resulting enone. This method is also suitable for the synthesis of meta- and ortho-disubstituted phenols, which have so far been especially difficult to access using existing synthetic methods.
The scope of the reaction was explored by combining different substituted -chlorocyclohexenones with a wide range of different boronic acids and boronate esters using optimized reaction conditions, leading to the synthesis of meta-substituted phenols in moderate to good yields.
Subject: Chemistry
Keywords: Chemistry
Organic chemistry
Synthetic chemistry
Synthesis
Phenols
Phenol synthesis
Cross-coupling
Oxidation
Suzuki
Suzuki-Miyaura
Aerobic oxidation
Boronic acid
Type: Electronic Thesis or Dissertation
Rights: Author owns copyright, except where explicitly noted. Please contact the author directly with licensing requests.
URI: http://hdl.handle.net/10315/34276
Supervisor: Garcia, Josue Arturo Orellana
Degree: MSc - Master of Science
Program: Chemistry
Exam date: 2017-04-20
Publish on: 2018-03-01

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