Diversity-Oriented Synthesis of Furo[3,2-c]coumarins and Benzofuranyl Chromenones through Chemoselective Acylation/Wittig Reaction

Shu Mei Yang; Chein Yi Wang; Chun Kai Lin; Praneeth Karanam; Ganapuram Madhusudhan Reddy; Yi Ling Tsai; Wenwei Lin

doi:10.1002/anie.201711524

Diversity-Oriented Synthesis of Furo[3,2-c]coumarins and Benzofuranyl Chromenones through Chemoselective Acylation/Wittig Reaction

Shu Mei Yang, Chein Yi Wang, Chun Kai Lin, Praneeth Karanam, Ganapuram Madhusudhan Reddy, Yi Ling Tsai, Wenwei Lin^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

22 Citations (Scopus)

Abstract

A highly efficient and chemoselective one-pot protocol for the diversity-oriented synthesis of two types of coumarin-based formal cross-coupling adducts, furo[3,2-c]coumarins and 3-benzofuranyl chromenones, is described. Key attributes of the methodology are an initial chemoselective acylation of functionalized phosphorus zwitterions and a subsequent chemoselective intramolecular Wittig reaction that preferentially resulted in one of the two coumarin derivatives in high yield, depending on relative reactivities and the addition sequence of the acylating agents.

Original language	English
Pages (from-to)	1668-1672
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	57
Issue number	6
DOIs	https://doi.org/10.1002/anie.201711524
Publication status	Published - 2018 Feb 5

Keywords

Wittig reactions
chemoselectivity
diversity-oriented synthesis
multicomponent reactions
organophosphonium salts

ASJC Scopus subject areas

Catalysis
Chemistry(all)

Access to Document

10.1002/anie.201711524

Cite this

Diversity-Oriented Synthesis of Furo[3,2-c]coumarins and Benzofuranyl Chromenones through Chemoselective Acylation/Wittig Reaction. / Yang, Shu Mei; Wang, Chein Yi; Lin, Chun Kai; Karanam, Praneeth; Reddy, Ganapuram Madhusudhan; Tsai, Yi Ling; Lin, Wenwei.

In: Angewandte Chemie - International Edition, Vol. 57, No. 6, 05.02.2018, p. 1668-1672.

Research output: Contribution to journal › Article › peer-review

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title = "Diversity-Oriented Synthesis of Furo[3,2-c]coumarins and Benzofuranyl Chromenones through Chemoselective Acylation/Wittig Reaction",

abstract = "A highly efficient and chemoselective one-pot protocol for the diversity-oriented synthesis of two types of coumarin-based formal cross-coupling adducts, furo[3,2-c]coumarins and 3-benzofuranyl chromenones, is described. Key attributes of the methodology are an initial chemoselective acylation of functionalized phosphorus zwitterions and a subsequent chemoselective intramolecular Wittig reaction that preferentially resulted in one of the two coumarin derivatives in high yield, depending on relative reactivities and the addition sequence of the acylating agents.",

keywords = "Wittig reactions, chemoselectivity, diversity-oriented synthesis, multicomponent reactions, organophosphonium salts",

author = "Yang, {Shu Mei} and Wang, {Chein Yi} and Lin, {Chun Kai} and Praneeth Karanam and Reddy, {Ganapuram Madhusudhan} and Tsai, {Yi Ling} and Wenwei Lin",

note = "Funding Information: We thank the Ministry of Science and Technology of the Republic of China (MOST 104-2113-M-003-002-MY3) for financial support. Publisher Copyright: {\textcopyright} 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

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AU - Lin, Chun Kai

AU - Karanam, Praneeth

AU - Reddy, Ganapuram Madhusudhan

AU - Tsai, Yi Ling

AU - Lin, Wenwei

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Y1 - 2018/2/5

N2 - A highly efficient and chemoselective one-pot protocol for the diversity-oriented synthesis of two types of coumarin-based formal cross-coupling adducts, furo[3,2-c]coumarins and 3-benzofuranyl chromenones, is described. Key attributes of the methodology are an initial chemoselective acylation of functionalized phosphorus zwitterions and a subsequent chemoselective intramolecular Wittig reaction that preferentially resulted in one of the two coumarin derivatives in high yield, depending on relative reactivities and the addition sequence of the acylating agents.

AB - A highly efficient and chemoselective one-pot protocol for the diversity-oriented synthesis of two types of coumarin-based formal cross-coupling adducts, furo[3,2-c]coumarins and 3-benzofuranyl chromenones, is described. Key attributes of the methodology are an initial chemoselective acylation of functionalized phosphorus zwitterions and a subsequent chemoselective intramolecular Wittig reaction that preferentially resulted in one of the two coumarin derivatives in high yield, depending on relative reactivities and the addition sequence of the acylating agents.

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Diversity-Oriented Synthesis of Furo[3,2-c]coumarins and Benzofuranyl Chromenones through Chemoselective Acylation/Wittig Reaction

Abstract

Keywords

ASJC Scopus subject areas

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CCDC 1484126: Experimental Crystal Structure Determination

CCDC 1401438: Experimental Crystal Structure Determination

CCDC 1401435: Experimental Crystal Structure Determination

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Diversity-Oriented Synthesis of Furo[3,2-c]coumarins and Benzofuranyl Chromenones through Chemoselective Acylation/Wittig Reaction

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 1484126: Experimental Crystal Structure Determination

CCDC 1401438: Experimental Crystal Structure Determination

CCDC 1401435: Experimental Crystal Structure Determination

Cite this