Synlett 2013; 24(15): 1993-1997
DOI: 10.1055/s-0033-1339690
letter
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 3-(Diarylmethylene)oxindoles via a Palladium-Catalyzed One-Pot Reaction: Sonogashira–Heck–Suzuki–Miyaura Combined Reaction

Guang Ri Dong
Integrated Research Institute of Pharmaceutical Sciences, College of Pharmacy, The Catholic University of Korea, 43 Jibong-ro, Wonmi-gu, Bucheon, Gyeonggi-do 420-743, Republic of Korea   Fax: +82(2)21644059   Email: [email protected]
,
Sunhwa Park
Integrated Research Institute of Pharmaceutical Sciences, College of Pharmacy, The Catholic University of Korea, 43 Jibong-ro, Wonmi-gu, Bucheon, Gyeonggi-do 420-743, Republic of Korea   Fax: +82(2)21644059   Email: [email protected]
,
Dahye Lee
Integrated Research Institute of Pharmaceutical Sciences, College of Pharmacy, The Catholic University of Korea, 43 Jibong-ro, Wonmi-gu, Bucheon, Gyeonggi-do 420-743, Republic of Korea   Fax: +82(2)21644059   Email: [email protected]
,
Kye Jung Shin
Integrated Research Institute of Pharmaceutical Sciences, College of Pharmacy, The Catholic University of Korea, 43 Jibong-ro, Wonmi-gu, Bucheon, Gyeonggi-do 420-743, Republic of Korea   Fax: +82(2)21644059   Email: [email protected]
,
Jae Hong Seo*
Integrated Research Institute of Pharmaceutical Sciences, College of Pharmacy, The Catholic University of Korea, 43 Jibong-ro, Wonmi-gu, Bucheon, Gyeonggi-do 420-743, Republic of Korea   Fax: +82(2)21644059   Email: [email protected]
› Author Affiliations
Further Information

Publication History

Received: 26 May 2013

Accepted after revision: 27 June 2013

Publication Date:
13 August 2013 (online)


Dedicated with respect to Professor Deukjoon Kim on the occasion of his 65th birthday

Abstract

A novel one-pot reaction for the synthesis of 3-(diarylmethylene)oxindoles is described. The reaction involves the successive combination of three palladium-catalyzed reactions (Sonogashira, Heck, and Suzuki–Miyaura reactions). This method enables the rapid synthesis of various 3-(diarylmethylene)oxindoles from simple propiolamides. The addition of silver salts dramatically enhanced the E/Z stereoselectivity of the reaction.

Supporting Information

 
  • References and Notes

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