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^*

^*此作品的通信作者

化學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

39 引文斯高帕斯（Scopus）

摘要

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.

原文	英語
頁（從 - 到）	1668-1672
頁數	5
期刊	Angewandte Chemie - International Edition
卷	57
發行號	6
DOIs	https://doi.org/10.1002/anie.201711524
出版狀態	已發佈 - 2018 2月 5

ASJC Scopus subject areas

催化
一般化學

存取文件

10.1002/anie.201711524

其它文件與鏈接

Link to publication in Scopus

CCDC 1484672: Experimental Crystal Structure Determination
Yang, S. (Creator), Wang, C. (Creator), Lin, C. (Creator), Karanam, P. (Creator), Reddy, G. M. (Creator), Tsai, Y. (Creator) & Lin, W. (Creator), Unknown Publisher, 2018
DOI: 10.5517/ccdc.csd.cc1ltxnz, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1ltxnz&sid=DataCite
資料集: Dataset
CCDC 1577534: Experimental Crystal Structure Determination
Yang, S. (Creator), Wang, C. (Creator), Lin, C. (Creator), Karanam, P. (Creator), Reddy, G. M. (Creator), Tsai, Y. (Creator) & Lin, W. (Creator), Unknown Publisher, 2018
DOI: 10.5517/ccdc.csd.cc1pyk6d, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1pyk6d&sid=DataCite
資料集: Dataset
CCDC 1484126: Experimental Crystal Structure Determination
Yang, S. (Creator), Wang, C. (Creator), Lin, C. (Creator), Karanam, P. (Creator), Reddy, G. M. (Creator), Tsai, Y. (Creator) & Lin, W. (Creator), Unknown Publisher, 2018
DOI: 10.5517/ccdc.csd.cc1ltc1t, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1ltc1t&sid=DataCite
資料集: Dataset

引用此

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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.",

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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",

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AU - Wang, Chein Yi

AU - Lin, Chun Kai

AU - Karanam, Praneeth

AU - Reddy, Ganapuram Madhusudhan

AU - Tsai, Yi Ling

AU - Lin, Wenwei

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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.

KW - Wittig reactions

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KW - multicomponent reactions

KW - organophosphonium salts

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

摘要

ASJC Scopus subject areas

存取文件

其它文件與鏈接

指紋

資料集

CCDC 1484672: Experimental Crystal Structure Determination

CCDC 1577534: Experimental Crystal Structure Determination

CCDC 1484126: Experimental Crystal Structure Determination

引用此