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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 44, 2014 - Issue 14
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Original Articles

Simple, Copper(I)-Catalyzed Oxidation of Benzylic/Allylic Alcohols to Carbonyl Compounds: Synthesis of Functionalized Cinnamates in One Pot

, &
Pages 2076-2087 | Received 11 Oct 2013, Published online: 09 Jun 2014
 

Abstract

An environmentally benign [Cu(I)]-catalyzed oxidation of activated (benzylic/allylic) alcohols to the corresponding carbonyl compounds is presented. Interestingly, the reaction was also compatible with benzylic alcohols containing ortho-bromo substituents on the aromatic ring without competing with the expected intermolecular Buchwald coupling. Significantly, the catalytic system enables the synthesis of cinnamate-esters in a sequential domino one-pot fashion via oxidation followed by Wittig–Horner protocol.

GRAPHICAL ABSTRACT

Notes

a Isolated yield of chromatographically pure product.

b Reaction was not clean.

c Conversion of the reaction based on TLC.

d Reaction was carried out under an inert atmosphere.

e Reaction was performed under open-air conditions fitted with a condenser.

a All reactions were performed on 0.5-mmol scale of the starting material 1.

b Isolated yields of chromatographically pure products.

c Yields are based on the recovery of the starting material.

d Reactions were carried out on 1-g scale under open-air conditions; accordingly it took more time than that required for small scale.

e No reaction took place; only starting material recovered (80%). The first and second numbers in parentheses are isolated yields by the methods A and B, respectively.

a All reactions were performed on 0.5-mmol scale of the starting material 1.

b Isolated yields of chromatographically pure products 3.

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