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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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
Online AccessGet full text

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Abstract 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.
AbstractList 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.
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.
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 tBuONO to act as a powerful nitrogenating agent for terminal aryl alkynes is demonstrated.
Author Lupton, David W
Maiti, Debabrata
Dutta, Uttam
AuthorAffiliation Department of Chemistry
Indian Institute of Technology Bombay
IITB-Monash Research Academy
IIT Bombay
Monash University
School of Chemistry
AuthorAffiliation_xml – name: Monash University
– name: Department of Chemistry
– name: Indian Institute of Technology Bombay
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– name: IIT Bombay
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Author_xml – sequence: 1
  givenname: Uttam
  surname: Dutta
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  givenname: David W
  surname: Lupton
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  email: david.lupton@monash.edu
– sequence: 3
  givenname: Debabrata
  surname: Maiti
  fullname: Maiti, Debabrata
  email: dmaiti@chem.iitb.ac.in
BackLink https://www.ncbi.nlm.nih.gov/pubmed/26849380$$D View this record in MEDLINE/PubMed
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Issue 4
Keywords 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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Snippet Alkyne CC bond breaking, outside of alkyne metathesis, remains an underdeveloped area in reaction discovery. Recently, nitrogenation has been reported to...
Alkyne C C bond breaking, outside of alkyne metathesis, remains an underdeveloped area in reaction discovery. Recently, nitrogenation has been reported to...
Alkyne C≡C bond breaking, outside of alkyne metathesis, remains an underdeveloped area in reaction discovery. Recently, nitrogenation has been reported to...
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SubjectTerms Chemistry
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Title Aryl Nitriles from Alkynes Using tert-Butyl Nitrite: Metal-Free Approach to CC Bond Cleavage
URI http://dx.doi.org/10.1021/acs.orglett.6b00147
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