Aryl Nitriles from Alkynes Using tert-Butyl Nitrite: Metal-Free Approach to CC Bond Cleavage

Alkyne CC bond breaking, outside of alkyne metathesis, remains an underdeveloped area in reaction discovery. Recently, nitrogenation has been reported to allow nitrile formation from alkynes. A new protocol for the metal-free CC bond cleavage of terminal alkynes to produce nitriles is reported. Th...

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Bibliographic Details
Published inOrganic letters Vol. 18; no. 4; pp. 860 - 863
Main Authors Dutta, Uttam, Lupton, David W, Maiti, Debabrata
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.02.2016
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
AMBIENT CONDITIONS
ANTI-MARKOVNIKOV HYDRATION
CATALYZED CYCLOADDITION
1,3-DIPOLAR CYCLOADDITION
SONOGASHIRA REACTION
TERMINAL ALKYNES
CARBON TRIPLE BOND
RADICAL-ADDITION
STEREOSELECTIVE NITRATION
MOLECULAR-OXYGEN
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Summary:Alkyne CC bond breaking, outside of alkyne metathesis, remains an underdeveloped area in reaction discovery. Recently, nitrogenation has been reported to allow nitrile formation from alkynes. A new protocol for the metal-free CC bond cleavage of terminal alkynes to produce nitriles is reported. This method provides an opportunity to synthesize a vast range of nitriles containing aryl, heteroaryl, and natural product derivatives (38 examples). In addition, the potential of t BuONO to act as a powerful nitrogenating agent for terminal aryl alkynes is demonstrated.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b00147