Cyanides-Free Cyanation of Aryl Halides using Formamide

A novel method for cyanation of aryl halides using formamide as a non‐toxic cyanide source is reported. It is a single‐step, solvent‐free method wherein formamide itself acts as solvent as well as source of cyanide in the presence of phosphorus oxychloride and palladium acetate/xantphos catalyst. Ar...

Full description

Saved in:
Bibliographic Details
Published in:Advanced synthesis & catalysis 2011-03, Vol.353 (5), p.781-787
Main Authors: Sawant, Dinesh N., Wagh, Yogesh S., Tambade, Pawan J., Bhatte, Kushal D., Bhanage, Bhalchandra M.
Format: Article
Language:English
Subjects:
Aromatic compounds
aryl halides
Catalysis
Catalysts: preparations and properties
Chemistry
cyanation
Cyanides
CC coupling
Exact sciences and technology
formamide
General and physical chemistry
Halides
Iodides
Kinetics and mechanisms
nitriles
Organic chemistry
Palladium
Reactivity and mechanisms
Solvents
Synthesis
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-c4567-d05af933189409f07a8607c096120dc3516ad8286ea7054194c9e1dfb83367383
cites cdi_FETCH-LOGICAL-c4567-d05af933189409f07a8607c096120dc3516ad8286ea7054194c9e1dfb83367383
container_end_page 787
container_issue 5
container_start_page 781
container_title Advanced synthesis & catalysis
container_volume 353
creator Sawant, Dinesh N.
Wagh, Yogesh S.
Tambade, Pawan J.
Bhatte, Kushal D.
Bhanage, Bhalchandra M.
description A novel method for cyanation of aryl halides using formamide as a non‐toxic cyanide source is reported. It is a single‐step, solvent‐free method wherein formamide itself acts as solvent as well as source of cyanide in the presence of phosphorus oxychloride and palladium acetate/xantphos catalyst. Aryl iodides as well as aryl bromides provided moderate to excellent yields of up to 93%.
doi_str_mv 10.1002/adsc.201000807
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1031293792</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1031293792</sourcerecordid><originalsourceid>FETCH-LOGICAL-c4567-d05af933189409f07a8607c096120dc3516ad8286ea7054194c9e1dfb83367383</originalsourceid><addsrcrecordid>eNqFkDtPwzAUhSMEEqWwMmdBYkm5juPXWFLagqoixGu0jOMgQx7FbgX59yRKFbEx-fj6O-fKJwjOEUwQQHylMq8nMbQaOLCDYIQoIlGCqDgcNIHj4MT7DwDEOGOjgKWNqmxmfDR3xoTdTW1tXYV1Hk5dU4RLVXTP4c7b6j2c165UZTs4DY5yVXhztj_HwfP85ildRqv7xW06XUU6IZRFGRCVC4wRFwmIHJjiFJgGQVEMmcYEUZXxmFOjGJAEiUQLg7L8jWNMGeZ4HFz2uRtXf-2M38rSem2KQlWm3nmJAKNYYCbiFp30qHa1987kcuNsqVzTQrJrSHYNyaGh1nCxz1ZeqyJ3qtLWD64YC04YJy0neu7bFqb5J1VOZ4_p3x1R77V-a34Gr3Kfsv0fI_J1vZCzu_Th-mW9kin-BSNTg4k</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1031293792</pqid></control><display><type>article</type><title>Cyanides-Free Cyanation of Aryl Halides using Formamide</title><source>Wiley</source><creator>Sawant, Dinesh N. ; Wagh, Yogesh S. ; Tambade, Pawan J. ; Bhatte, Kushal D. ; Bhanage, Bhalchandra M.</creator><creatorcontrib>Sawant, Dinesh N. ; Wagh, Yogesh S. ; Tambade, Pawan J. ; Bhatte, Kushal D. ; Bhanage, Bhalchandra M.</creatorcontrib><description>A novel method for cyanation of aryl halides using formamide as a non‐toxic cyanide source is reported. It is a single‐step, solvent‐free method wherein formamide itself acts as solvent as well as source of cyanide in the presence of phosphorus oxychloride and palladium acetate/xantphos catalyst. Aryl iodides as well as aryl bromides provided moderate to excellent yields of up to 93%.</description><identifier>ISSN: 1615-4150</identifier><identifier>ISSN: 1615-4169</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.201000807</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Aromatic compounds ; aryl halides ; Catalysis ; Catalysts: preparations and properties ; Chemistry ; cyanation ; Cyanides ; CC coupling ; Exact sciences and technology ; formamide ; General and physical chemistry ; Halides ; Iodides ; Kinetics and mechanisms ; nitriles ; Organic chemistry ; Palladium ; Reactivity and mechanisms ; Solvents ; Synthesis ; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</subject><ispartof>Advanced synthesis &amp; catalysis, 2011-03, Vol.353 (5), p.781-787</ispartof><rights>Copyright © 2011 WILEY‐VCH Verlag GmbH &amp; Co. KGaA, Weinheim</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4567-d05af933189409f07a8607c096120dc3516ad8286ea7054194c9e1dfb83367383</citedby><cites>FETCH-LOGICAL-c4567-d05af933189409f07a8607c096120dc3516ad8286ea7054194c9e1dfb83367383</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&amp;idt=23985785$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Sawant, Dinesh N.</creatorcontrib><creatorcontrib>Wagh, Yogesh S.</creatorcontrib><creatorcontrib>Tambade, Pawan J.</creatorcontrib><creatorcontrib>Bhatte, Kushal D.</creatorcontrib><creatorcontrib>Bhanage, Bhalchandra M.</creatorcontrib><title>Cyanides-Free Cyanation of Aryl Halides using Formamide</title><title>Advanced synthesis &amp; catalysis</title><addtitle>Adv. Synth. Catal</addtitle><description>A novel method for cyanation of aryl halides using formamide as a non‐toxic cyanide source is reported. It is a single‐step, solvent‐free method wherein formamide itself acts as solvent as well as source of cyanide in the presence of phosphorus oxychloride and palladium acetate/xantphos catalyst. Aryl iodides as well as aryl bromides provided moderate to excellent yields of up to 93%.</description><subject>Aromatic compounds</subject><subject>aryl halides</subject><subject>Catalysis</subject><subject>Catalysts: preparations and properties</subject><subject>Chemistry</subject><subject>cyanation</subject><subject>Cyanides</subject><subject>CC coupling</subject><subject>Exact sciences and technology</subject><subject>formamide</subject><subject>General and physical chemistry</subject><subject>Halides</subject><subject>Iodides</subject><subject>Kinetics and mechanisms</subject><subject>nitriles</subject><subject>Organic chemistry</subject><subject>Palladium</subject><subject>Reactivity and mechanisms</subject><subject>Solvents</subject><subject>Synthesis</subject><subject>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</subject><issn>1615-4150</issn><issn>1615-4169</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><recordid>eNqFkDtPwzAUhSMEEqWwMmdBYkm5juPXWFLagqoixGu0jOMgQx7FbgX59yRKFbEx-fj6O-fKJwjOEUwQQHylMq8nMbQaOLCDYIQoIlGCqDgcNIHj4MT7DwDEOGOjgKWNqmxmfDR3xoTdTW1tXYV1Hk5dU4RLVXTP4c7b6j2c165UZTs4DY5yVXhztj_HwfP85ildRqv7xW06XUU6IZRFGRCVC4wRFwmIHJjiFJgGQVEMmcYEUZXxmFOjGJAEiUQLg7L8jWNMGeZ4HFz2uRtXf-2M38rSem2KQlWm3nmJAKNYYCbiFp30qHa1987kcuNsqVzTQrJrSHYNyaGh1nCxz1ZeqyJ3qtLWD64YC04YJy0neu7bFqb5J1VOZ4_p3x1R77V-a34Gr3Kfsv0fI_J1vZCzu_Th-mW9kin-BSNTg4k</recordid><startdate>20110328</startdate><enddate>20110328</enddate><creator>Sawant, Dinesh N.</creator><creator>Wagh, Yogesh S.</creator><creator>Tambade, Pawan J.</creator><creator>Bhatte, Kushal D.</creator><creator>Bhanage, Bhalchandra M.</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley-VCH</general><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20110328</creationdate><title>Cyanides-Free Cyanation of Aryl Halides using Formamide</title><author>Sawant, Dinesh N. ; Wagh, Yogesh S. ; Tambade, Pawan J. ; Bhatte, Kushal D. ; Bhanage, Bhalchandra M.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4567-d05af933189409f07a8607c096120dc3516ad8286ea7054194c9e1dfb83367383</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Aromatic compounds</topic><topic>aryl halides</topic><topic>Catalysis</topic><topic>Catalysts: preparations and properties</topic><topic>Chemistry</topic><topic>cyanation</topic><topic>Cyanides</topic><topic>CC coupling</topic><topic>Exact sciences and technology</topic><topic>formamide</topic><topic>General and physical chemistry</topic><topic>Halides</topic><topic>Iodides</topic><topic>Kinetics and mechanisms</topic><topic>nitriles</topic><topic>Organic chemistry</topic><topic>Palladium</topic><topic>Reactivity and mechanisms</topic><topic>Solvents</topic><topic>Synthesis</topic><topic>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sawant, Dinesh N.</creatorcontrib><creatorcontrib>Wagh, Yogesh S.</creatorcontrib><creatorcontrib>Tambade, Pawan J.</creatorcontrib><creatorcontrib>Bhatte, Kushal D.</creatorcontrib><creatorcontrib>Bhanage, Bhalchandra M.</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Advanced synthesis &amp; catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sawant, Dinesh N.</au><au>Wagh, Yogesh S.</au><au>Tambade, Pawan J.</au><au>Bhatte, Kushal D.</au><au>Bhanage, Bhalchandra M.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Cyanides-Free Cyanation of Aryl Halides using Formamide</atitle><jtitle>Advanced synthesis &amp; catalysis</jtitle><addtitle>Adv. Synth. Catal</addtitle><date>2011-03-28</date><risdate>2011</risdate><volume>353</volume><issue>5</issue><spage>781</spage><epage>787</epage><pages>781-787</pages><issn>1615-4150</issn><issn>1615-4169</issn><eissn>1615-4169</eissn><abstract>A novel method for cyanation of aryl halides using formamide as a non‐toxic cyanide source is reported. It is a single‐step, solvent‐free method wherein formamide itself acts as solvent as well as source of cyanide in the presence of phosphorus oxychloride and palladium acetate/xantphos catalyst. Aryl iodides as well as aryl bromides provided moderate to excellent yields of up to 93%.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/adsc.201000807</doi><tpages>7</tpages></addata></record>
fulltext fulltext
identifier ISSN: 1615-4150
ispartof Advanced synthesis & catalysis, 2011-03, Vol.353 (5), p.781-787
issn 1615-4150
1615-4169
1615-4169
language eng
recordid cdi_proquest_miscellaneous_1031293792
source Wiley
subjects Aromatic compounds
aryl halides
Catalysis
Catalysts: preparations and properties
Chemistry
cyanation
Cyanides
CC coupling
Exact sciences and technology
formamide
General and physical chemistry
Halides
Iodides
Kinetics and mechanisms
nitriles
Organic chemistry
Palladium
Reactivity and mechanisms
Solvents
Synthesis
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
title Cyanides-Free Cyanation of Aryl Halides using Formamide
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-02T16%3A08%3A42IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Cyanides-Free%20Cyanation%20of%20Aryl%20Halides%20using%20Formamide&rft.jtitle=Advanced%20synthesis%20&%20catalysis&rft.au=Sawant,%20Dinesh%20N.&rft.date=2011-03-28&rft.volume=353&rft.issue=5&rft.spage=781&rft.epage=787&rft.pages=781-787&rft.issn=1615-4150&rft.eissn=1615-4169&rft_id=info:doi/10.1002/adsc.201000807&rft_dat=%3Cproquest_cross%3E1031293792%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c4567-d05af933189409f07a8607c096120dc3516ad8286ea7054194c9e1dfb83367383%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=1031293792&rft_id=info:pmid/&rfr_iscdi=true