Improving Robustness: In Situ Generation of a Pd(0) Catalyst for the Cyanation of Aryl Bromides

Conditions have been developed for the palladium-catalyzed cyanation of aryl bromides utilizing the air-stable XantPhos-PdCl2 precatalyst. By employing a trialkylamine as a reducing agent, the active Pd(0) species is generated in situ, alleviating the need to employ the air-sensitive Pd2(dba)3. Twen...

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Published inJournal of organic chemistry Vol. 82; no. 13; pp. 7040 - 7044
Main Authors Coombs, John R, Fraunhoffer, Kenneth J, Simmons, Eric M, Stevens, Jason M, Wisniewski, Steven R, Yu, Miao
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.07.2017
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
HALIDES
AGENT
MILD
SYSTEM
PALLADIUM
NITRILES
CHLORIDES
HALOARENES
POTASSIUM HEXACYANOFERRATE(II)
BENZONITRILES
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Summary:Conditions have been developed for the palladium-catalyzed cyanation of aryl bromides utilizing the air-stable XantPhos-PdCl2 precatalyst. By employing a trialkylamine as a reducing agent, the active Pd(0) species is generated in situ, alleviating the need to employ the air-sensitive Pd2(dba)3. Twenty-two substituted benzonitriles have been synthesized using this method.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b01003