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

Guang Ri Dong; Sunhwa Park; Dahye Lee; Kye Jung Shin; Jae Hong Seo

doi:10.1055/s-0033-1339690

Synlett, Table of Contents

Synlett 2013; 24(15): 1993-1997
DOI: 10.1055/s-0033-1339690

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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: jaehongseo@catholic.ac.kr

,

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: jaehongseo@catholic.ac.kr

,

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: jaehongseo@catholic.ac.kr

,

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: jaehongseo@catholic.ac.kr

,

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: jaehongseo@catholic.ac.kr

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Abstract

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

Key words

palladium - stereoselectivity - Heck reaction - Sonogashira reaction - oxindole

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References

References and Notes

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Supplementary Material

Supporting Information