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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

Palladium-Catalyzed Selective α-Arylation of ortho-Bromoacetophenones

, &
Pages 2103-2111 | Received 11 Oct 2013, Published online: 09 Jun 2014
 

Abstract

Synthesis of 1-(2-bromophenyl)-2-phenylethanones via an intermolecular Pd-catalyzed α-arylation of 1-(2-bromophenyl)ethanones is presented. The method relies on selective C-H activation (α-arylation) of relatively more reactive external iodo-arenes as coupling partners without affecting the bromo-substituent. Moreover, the scope and generality of the method has been well studied by employing the reaction with iodo-arenes as coupling partners bearing electron-withdrawing, simple, and electron-donating groups on the aromatic ring.

GRAPHICAL ABSTRACT

Notes

a All reactions are carried out on 0.5-mmol scale of iodo-arenes in 4 mL of toluene (0.12 M).

b Yields in the parentheses are isolated yields of chromatographically pure products.

c For compounds 3ac3cf the first letter refers to the 2-bromoacetophenes 1a1c, whereas the second letter indicates the aromatic ring coming from iodo-arenes 2a2f.

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