Microwave-Promoted Pd-Catalyzed Cyanation of Aryl Triflates:  A Fast and Versatile Access to 3-Cyano-3-desoxy-10-ketomorphinans

Microwave-Promoted Pd-Catalyzed Cyanation of Aryl Triflates:  A Fast and Versatile Access to 3-Cyano-3-desoxy-10-ketomorphinans

A methodology for the microwave-promoted conversion of triflates to the corresponding nitriles by using 8% equiv of Pd(Ph3P)4 as the catalyst and 2.0 equiv of Zn(CN)2 as the cyanide source has been developed. This method is highly efficient for the preparation of 3-cyano-3-desoxy-10-ketomorphinans....

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Veröffentlicht in:Organic letters 2003-01, Vol.5 (2), p.201-203
Hauptverfasser: Zhang, Ao, Neumeyer, John L
Format: Artikel
Sprache:eng
Schlagworte:
Catalysis
Cyanides - chemistry
Ligands
Mesylates - chemistry
Microwaves
Narcotic Antagonists
Nitriles - chemical synthesis
Palladium
Receptors, Opioid - agonists
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creator Zhang, Ao
Neumeyer, John L
description A methodology for the microwave-promoted conversion of triflates to the corresponding nitriles by using 8% equiv of Pd(Ph3P)4 as the catalyst and 2.0 equiv of Zn(CN)2 as the cyanide source has been developed. This method is highly efficient for the preparation of 3-cyano-3-desoxy-10-ketomorphinans. The reaction was generally completed in 15 min at 200 °C and produced products in greater than 86% yields.
doi_str_mv 10.1021/ol027256p
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The reaction was generally completed in 15 min at 200 °C and produced products in greater than 86% yields.</description><subject>Catalysis</subject><subject>Cyanides - chemistry</subject><subject>Ligands</subject><subject>Mesylates - chemistry</subject><subject>Microwaves</subject><subject>Narcotic Antagonists</subject><subject>Nitriles - chemical synthesis</subject><subject>Palladium</subject><subject>Receptors, Opioid - agonists</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkLtOwzAUhi0E4lIYeAHkBSQGg-0kNmarKm4SiA7AGp0kJyKQxsV2gTDByGvyJBi1goXpXPTpOzo_IduCHwguxaFtudQyU9Mlsi4ymTDNM7n82yu-Rja8f-BcxI1ZJWtCxipSvk4-rprS2Rd4RjZ2dmIDVnRcsREEaPu3OIx66CA0tqO2pkPXt_TGNXULAf3x1_snHdJT8IFCV9E7dD6iLdJhWaL3NFiasB-BZQmr0NvXngnOHjHES25633TQ-U2yUkPrcWtRB-T29ORmdM4ur88uRsNLBokQgekjSEyFBiuTJljwVCmJqZRcqgyOCq4zWSsjM41KAShdZcKAMVAIUehaiGRA9ubeqbNPM_QhnzS-xLaFDu3M51oarXmaRnB_DsZgvHdY51PXTMD1ueD5T975b96R3VlIZ8UEqz9yEXAEducAlD5_sDPXxR__EX0D6cuHMQ</recordid><startdate>20030123</startdate><enddate>20030123</enddate><creator>Zhang, Ao</creator><creator>Neumeyer, John L</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20030123</creationdate><title>Microwave-Promoted Pd-Catalyzed Cyanation of Aryl Triflates:  A Fast and Versatile Access to 3-Cyano-3-desoxy-10-ketomorphinans</title><author>Zhang, Ao ; Neumeyer, John L</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a311t-78a39de9ed943eb04662e4220265a8b0752f69257e66aa67d519a99ab11b7f113</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>Catalysis</topic><topic>Cyanides - chemistry</topic><topic>Ligands</topic><topic>Mesylates - chemistry</topic><topic>Microwaves</topic><topic>Narcotic Antagonists</topic><topic>Nitriles - chemical synthesis</topic><topic>Palladium</topic><topic>Receptors, Opioid - agonists</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhang, Ao</creatorcontrib><creatorcontrib>Neumeyer, John L</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhang, Ao</au><au>Neumeyer, John L</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Microwave-Promoted Pd-Catalyzed Cyanation of Aryl Triflates:  A Fast and Versatile Access to 3-Cyano-3-desoxy-10-ketomorphinans</atitle><jtitle>Organic letters</jtitle><addtitle>Org. 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subjects Catalysis
Cyanides - chemistry
Ligands
Mesylates - chemistry
Microwaves
Narcotic Antagonists
Nitriles - chemical synthesis
Palladium
Receptors, Opioid - agonists
title Microwave-Promoted Pd-Catalyzed Cyanation of Aryl Triflates:  A Fast and Versatile Access to 3-Cyano-3-desoxy-10-ketomorphinans
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