Cascade Transformations of [1,2,3]Triazolo[1,5-a]pyridines as Convenient Precursors of Diazo Compounds and Metal Carbenes

The cyclopropanation of alkenes through the transition-metal-catalyzed decomposition of diazo compounds is a powerful and straightforward strategy to produce cyclopropanes. Nevertheless, the appeal of further application of this strategy is tempered by the potentially explosive nature of the diazo substrates. Therefore, it is highly desirable to develop sustainable and operationally safe surrogates for diazo compounds. In this synpacts article, we discuss recent advances on the cyclopropane syntheses through the catalytic cyclopropanation of alkenes and metal-carbenes generated in-situ from non-diazo precursors, as well as highlight our recent progress on the unprecedented molybdenum-catalyzed deoxygenative cyclopropanation reaction of 1,2-dicarbonyl or monocarbonyl compounds.

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Correlations between catalytic reactions of diazo compounds and stoichiometric reactions of transition-metal carbenes with alkenes. Mechanism of the cyclopropanation reaction

Organometallics ◽

10.1021/om00079a011 ◽

1984 ◽

Vol 3 (1) ◽

pp. 53-61 ◽

Cited By ~ 143

Author(s):

Michael P. Doyle ◽

John H. Griffin ◽

Vahid Bagheri ◽

Roberta L. Dorow

Keyword(s):

Transition Metal ◽

Catalytic Reactions ◽

Diazo Compounds ◽

Metal Carbenes

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Recent Progress in N-Heterocyclic Carbene Gold-Catalyzed Reactions of Alkynes Involving Oxidation/Amination/Cycloaddition

Catalysts ◽

10.3390/catal10030350 ◽

2020 ◽

Vol 10 (3) ◽

pp. 350 ◽

Cited By ~ 7

Author(s):

Xiang-Ting Tang ◽

Fan Yang ◽

Ting-Ting Zhang ◽

Yi-Fan Liu ◽

Si-Yu Liu ◽

...

Keyword(s):

Recent Progress ◽

Rapid Development ◽

Gold Catalysis ◽

Diazo Compounds ◽

Ancillary Ligands ◽

Metal Carbenes ◽

Directing Group ◽

Catalyzed Reactions ◽

Exciting Area ◽

Catalyzed Oxidation

Recent rapid development in homogeneous gold catalysis affords an alternative and particularly thriving strategy for the generation of gold carbenes through gold-catalyzed oxidation/amination/cycloaddition of alkynes, while it avoids the employment of hazardous and potentially explosive diazo compounds as starting materials for carbene generation. In addition to facile and secure operation, gold carbenes generated in this strategy display good chemoselectivity distinct from other metal carbenes produced from the related diazo approach. N-heterocyclic carbene (NHC) gold is a special metal complex that can be used as ancillary ligands, which provides enhanced stability and can also act as an efficient chiral directing group. In this review, we will present an overview of these recent advances in alkyne oxidation/amination/cycloaddition by highlighting their specificity and applicability, aiming to facilitate progress in this very exciting area of research.

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Recent progress towards the transition-metal-catalyzed Nazarov cyclization of alkynes via metal carbenes

Organic & Biomolecular Chemistry ◽

10.1039/d1ob00744k ◽

2021 ◽

Author(s):

Wen-Bo Shen ◽

Guang-Xin Ru ◽

Ting-Ting Zhang ◽

Meng Zhang ◽

Xiao-Lei Jiang ◽

...

Keyword(s):

Transition Metal ◽

Recent Progress ◽

Cyclization Reaction ◽

Diazo Compounds ◽

Nazarov Cyclization ◽

Metal Carbenes ◽

Transition Metal Catalyzed ◽

Tandem Cyclization ◽

Metal Catalyzed

In recent years, transition-metal-catalyzed tandem cyclization reaction of alkyne, especially involving metal carbene intermediate, has received worthwhile interest as it bypasses the employment of risky and potentially explosive diazo compounds...

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