Alkynylation of benzonitriles via nickel catalyzed C–C bond activation

Penney, Jonathan M.; Miller, Joseph A.

doi:10.1016/j.tetlet.2004.02.163

Cited by 70 publications

(25 citation statements)

References 4 publications

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“…2‐thiophenecarbonitrile, 2‐pyridinecarbonitrile) in >70 % yield. At present, the method cannot compete with the Kumada coupling7 using aryl halides, although aryl cyanides have found an elegant application in related reactions, in particular in the nickel‐catalyzed cross‐coupling with alkynylzinc6c and alkenyl Grignard6d reagents to form the corresponding aryl alkynes and aryl alkenes.…”

Section: Methodsmentioning

confidence: 99%

Biaryl Formation Involving Carbon‐Based Leaving Groups: Why Not?

2008

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Section: Methodsmentioning

confidence: 99%

Biaryl Formation Involving Carbon‐Based Leaving Groups: Why Not?

2008

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“…In sharp contrast, Ni‐catalyzed cross‐coupling reactions to incorporate alkynylzinc reagent for alkynylation reactions were quite efficient [45] . A variety of aryl nitriles and terminal alkynes participated efficiently to form various disubstituted acetylenes (Scheme 25).…”

Section: Decyanative Functionalizationmentioning

confidence: 99%

Recent Developments in Hydrodecyanation and Decyanative Functionalization Reactions

Paul

Patra

2021

Asian J Org Chem

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Nitrile is one of the ubiquitous functional groups in natural products and polymer industry. It is often used as a versatile building block in synthetic chemistry. Classically, nitrile group is used for alpha functionalization, orthoÀ CÀ H activation and as a precursor for amine or carbonyl functionalities. With the development of various transition metal catalyzed methods, in the last two decades, nitrile group has emerged as a source of carbon synthons through CÀ CN bond activation despite of its high bond energy. In this review we have summarized all recent developments involving the carbon synthons arising from the cleavage of CÀ CN bonds. Depending on the fate of the carbon center after cleavage, all the reactions are classified in two major categories for the ease of discussion: 1) decyanation (removal of the nitrile group) and 2) decyanative functionalization (replacement of the nitrile group). Finally, current limitations in CÀ CN bond activation strategies and future prospects are discussed.

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“…In particular, Miller et al have developed an efficient, novel procedure to prepare unsymmetrical biaryls, styrenes, and alkylated benzene derivatives by means of Nicatalyzed cross-coupling reactions starting from benzonitriles (see Scheme 13). [50] A survey of the catalysts indicated that [NiCl 2 A C H T U N G T R E N N U N G (PMe 3 ) 2 ] was generally superior to other Ni-or Pd-based catalytic systems and it also had the advantage of being commercially available. [50b] Organozinc and Grignard reagents were used as the nucleophiles.…”

Section: Cn As the Leaving Group (Activation Ofmentioning

confidence: 99%

The Aromatic Carbon–Carbon ipso‐Substitution Reaction

Bonesi

Fagnoni

2010

Chemistry A European J

130

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The aim of this review is to illustrate what we have dubbed an aromatic carbon-carbon ipso-substitution reaction in which a new Ar-C bond is formed at the expense of another Ar-C bond. The potentiality of several C-based leaving groups including alkyl, carbinol, CN, COOH, and carbonyl groups in arylation reactions will be illustrated accordingly for the preparation of biphenyl-, vinyl-, alkynyl-, and alkyl-substituted aromatics.

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Alkynylation of benzonitriles via nickel catalyzed C–C bond activation

Cited by 70 publications

References 4 publications

Biaryl Formation Involving Carbon‐Based Leaving Groups: Why Not?

Biaryl Formation Involving Carbon‐Based Leaving Groups: Why Not?

Recent Developments in Hydrodecyanation and Decyanative Functionalization Reactions

The Aromatic Carbon–Carbon ipso‐Substitution Reaction

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