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Palladium-Catalyzed One-Pot Synthesis of 2-Alkyl-2-arylcyanoacetates

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Xiang Wang,* Anil Guram, Emilio Bunel, Guo-Qiang Cao,^† Jennifer R. Allen,^† and Margaret M. Faul

Chemical Process R&D, Amgen Inc., One Amgen Center Drive, Thousand Oaks, California 91320 xiangw@amgen.com

J. Org. Chem., 2008, 73 (4), pp 1643–1645

DOI: 10.1021/jo7024338

Publication Date (Web): January 16, 2008

Section:

General Organic Chemistry

Abstract

A one-pot procedure for the synthesis of 2-alkyl-2-arylcyanoacetates based on a Pd(OAc)₂/DPPF (DPPF = 1,1‘-diphenylphosphino ferreocene)-catalyzed enolate arylation followed by in situ alkylation has been developed. This procedure tolerates a diverse range of aryl and heteroaryl bromides, and provides a rapid entry to a variety of 2-alkyl-2-arylcyanoacetates in good to excellent yield.

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This article has been cited by 1 ACS Journal articles (1 most recent appear below).

Synthesis of Substituted Isoquinolines via Pd-Catalyzed Cross-Coupling Approaches
Nick Todorovic, Emelia Awuah, Silvia Albu, Cory Ozimok, and Alfredo Capretta
Organic Letters2011 13 (23), 6180-6183
- Synthesis of Substituted Isoquinolines via Pd-Catalyzed Cross-Coupling Approaches
  Nick Todorovic, Emelia Awuah, Silvia Albu, Cory Ozimok, and Alfredo Capretta
  Organic Letters2011 13 (23), 6180-6183
  Palladium complexes incorporating ligands based on a 1,3,5,7-tetramethyl-2,4,8-trioxa-6-phosphaadamantanyl scaffold were used to catalyze the arylation of ethyl cyanoacetate, malononitrile, and various ketones. The products from these reactions can be ...
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Published In Issue February 15, 2008
Received November 13, 2007

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Note

Palladium-Catalyzed One-Pot Synthesis of 2-Alkyl-2-arylcyanoacetates

Abstract

Citing Articles

Synthesis of Substituted Isoquinolines via Pd-Catalyzed Cross-Coupling Approaches