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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 36, 2006 - Issue 20
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Original Articles

Suzuki Coupling of 2‐Chloroacrylonitrile, Methyl 2‐Chloroacrylate, or 2‐Chloroprop‐1‐en‐3‐ol with Arylboronic Acids Catalyzed by a Palladium‐Tetraphosphine Complex

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Pages 3019-3027 | Received 16 Mar 2006, Published online: 16 Feb 2007
 

Abstract

The tetraphosphine all‐cis‐1,2,3,4‐tetrakis(diphenylphosphinomethyl)cyclopentane (Tedicyp) in combination with [Pd(C3H5)Cl]2 affords an efficient catalyst of the coupling of 2‐chloroacrylonitrile with arylboronic acids. In the presence of 1% catalyst, the 2‐arylacrylonitrile derivatives were obtained in medium to good yields. A variety of substituents such as alkyl, methoxy, fluoro, trifluoromethyl, formyl, or nitro on the arylboronic acid are tolerated. The cross‐coupling reactions of methyl 2‐chloroacrylate with arylboronic acids give simple access to 2‐phenylacrylate derivatives, which are useful precursors for the synthesis of biologically active compounds such as ibuprofen, ketoprofen, and naproxen.

Acknowledgment

We thank the CNRS for providing financial support.

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