Synthesis of Cyclohexane-Fused Isocoumarins via Cationic Palladium(II)-Catalyzed Cascade Cyclization Reaction of Alkyne-Tethered Carbonyl Compounds Initiated by Intramolecular Oxypalladation of Ester-Substituted Aryl Alkynes

A cationic Pd(II)-catalyzed cascade cyclization reaction of alkyne-tethered carbonyl compounds was developed. This reaction is initiated by intramolecular oxypalladation of alkynes with an ester group followed by 1,2-addition of the formed C–Pd(II) bond to the carbonyl group, providing a highly ef...

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Veröffentlicht in:	Journal of organic chemistry 2016-04, Vol.81 (8), p.3423-3429
Hauptverfasser:	Zhang, Jianbo, Han, Xiuling, Lu, Xiyan
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkynes - chemistry Catalysis Cations - chemistry Cyclization Cyclohexanes - chemical synthesis Cyclohexanes - chemistry Esters Indoles - chemistry Isocoumarins - chemical synthesis Isocoumarins - chemistry Molecular Structure Palladium - chemistry
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container_title	Journal of organic chemistry
container_volume	81
creator	Zhang, Jianbo Han, Xiuling Lu, Xiyan
description	A cationic Pd(II)-catalyzed cascade cyclization reaction of alkyne-tethered carbonyl compounds was developed. This reaction is initiated by intramolecular oxypalladation of alkynes with an ester group followed by 1,2-addition of the formed C–Pd(II) bond to the carbonyl group, providing a highly efficient method for the synthesis of cyclohexane-fused isocoumarins.
doi_str_mv	10.1021/acs.joc.6b00128
format	Article
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Org. Chem</addtitle><date>2016-04-15</date><risdate>2016</risdate><volume>81</volume><issue>8</issue><spage>3423</spage><epage>3429</epage><pages>3423-3429</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>A cationic Pd(II)-catalyzed cascade cyclization reaction of alkyne-tethered carbonyl compounds was developed. This reaction is initiated by intramolecular oxypalladation of alkynes with an ester group followed by 1,2-addition of the formed C–Pd(II) bond to the carbonyl group, providing a highly efficient method for the synthesis of cyclohexane-fused isocoumarins.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>26999527</pmid><doi>10.1021/acs.joc.6b00128</doi><tpages>7</tpages></addata></record>
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subjects	Alkynes - chemistry Catalysis Cations - chemistry Cyclization Cyclohexanes - chemical synthesis Cyclohexanes - chemistry Esters Indoles - chemistry Isocoumarins - chemical synthesis Isocoumarins - chemistry Molecular Structure Palladium - chemistry
title	Synthesis of Cyclohexane-Fused Isocoumarins via Cationic Palladium(II)-Catalyzed Cascade Cyclization Reaction of Alkyne-Tethered Carbonyl Compounds Initiated by Intramolecular Oxypalladation of Ester-Substituted Aryl Alkynes
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