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

39 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
General Chemistry

Access to Document

10.1002/anie.201711524

Cite this

@article{1fc65353a28d46cba137f0385d9aad09,

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 = "Publisher Copyright: {\textcopyright} 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2018",

month = feb,

day = "5",

doi = "10.1002/anie.201711524",

language = "English",

volume = "57",

pages = "1668--1672",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "6",

}

TY - JOUR

T1 - Diversity-Oriented Synthesis of Furo[3,2-c]coumarins and Benzofuranyl Chromenones through Chemoselective Acylation/Wittig Reaction

AU - Yang, Shu Mei

AU - Wang, Chein Yi

AU - Lin, Chun Kai

AU - Karanam, Praneeth

AU - Reddy, Ganapuram Madhusudhan

AU - Tsai, Yi Ling

AU - Lin, Wenwei

PY - 2018/2/5

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.

KW - Wittig reactions

KW - chemoselectivity

KW - diversity-oriented synthesis

KW - multicomponent reactions

KW - organophosphonium salts

UR - http://www.scopus.com/inward/record.url?scp=85041031446&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85041031446&partnerID=8YFLogxK

U2 - 10.1002/anie.201711524

DO - 10.1002/anie.201711524

M3 - Article

C2 - 29206341

AN - SCOPUS:85041031446

SN - 1433-7851

VL - 57

SP - 1668

EP - 1672

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 6

ER -

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

CCDC 1484672: Experimental Crystal Structure Determination

CCDC 1577534: Experimental Crystal Structure Determination

CCDC 1484126: Experimental Crystal Structure Determination

Cite this

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 1484672: Experimental Crystal Structure Determination

CCDC 1577534: Experimental Crystal Structure Determination

CCDC 1484126: Experimental Crystal Structure Determination

Cite this