Microwave-Assisted, Pd(0)-Catalyzed Cross-Coupling of Diazirines with Aryl Halides

Zhao, Xia; Wu, Guojiao; Yan, Chong; Lu, Kui; Li, Hui; Zhang, Yan; Wang, Jianbo

doi:10.1021/ol102434v

Cited by 45 publications

(16 citation statements)

References 39 publications

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“…The use of diazo-compounds as efficient coupling partners for Pd-catalyzed C-C bond forming reactions has been described by Wang and co-workers. 56 They demonstrated that substituted diazirines can be efficiently cross-coupled with aromatic halides (Br or Cl) under microwave irradiation. The reactions were carried out employing Pd 2 (dba) 3 as a catalyst at a ceiling temperature of 110 1C for 10 min, affording substituted alkene derivatives in good yields (Scheme 32).…”

Section: Miscellaneous Reactionsmentioning

confidence: 99%

Microwave-assisted C–C bond forming cross-coupling reactions: an overview

2011

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Among the fundamental transformations in the field of synthetic organic chemistry, transition-metal-catalyzed reactions provide some of the most attractive methodologies for the formation of C-C and C-heteroatom bonds. As a result, the application of these reactions has increased tremendously during the past decades and cross-coupling reactions became a standard tool for synthetic organic chemists. Furthermore, a tremendous upsurge in the development of new catalysts and ligands, as well as an increased understanding of the mechanisms, has contributed substantially to recent advances in the field. Traditionally, organic reactions are carried out by conductive heating with an external heat source (for example, an oil bath). However, the application of microwave irradiation is a steadily gaining field as an alternative heating mode since its dawn at the end of the last century. This tutorial review focuses on some of the recent developments in the field of cross-coupling reactions assisted by microwave irradiation.

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Section: Miscellaneous Reactionsmentioning

confidence: 99%

Microwave-assisted C–C bond forming cross-coupling reactions: an overview

2011

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“…The reactivity of non-substituted diaziridines towards oxidants for the feasible synthesis of 3H-diazirines expands its applicability as an important intermediate. In a study exploring the process of Pd(0)-catalyzed cross-coupling of diazirines with aryl halides assisted by microwave irradiation [33], 3-methyl-3-(p-tolyl)diaziridine 14 was employed for the Pd(0)-catalyzed cross-coupling with 4-bromotoluene 15-resulting in the product 4,4'-(ethene-1,1-diyl)bis(methylbenzene) 16-under oxidative conditions following the addition of Ag 2 O as an oxidant (Scheme 1). The Pd(0)-catalyzed cross-coupling is the first example of a transition-metal-catalyzed reaction of diazirines supported by combination with the conventional oxidation of diaziridine, and significantly expands the chemistry of three-membered heterocycles.…”

Section: Conventional Methods For Recent Usesmentioning

confidence: 99%

New Trends in Diaziridine Formation and Transformation (a Review)

et al. 2021

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This review focuses on diaziridine, a high strained three-membered heterocycle with two nitrogen atoms that plays an important role as one of the most important precursors of diazirine photoaffinity probes, as well as their formation and transformation. Recent research trends can be grouped into three categories, based on whether they have examined non-substituted, N-monosubstituted, or N,N-disubstituted diaziridines. The discussion expands on the conventional methods for recent applications, the current spread of studies, and the unconventional synthesis approaches arising over the last decade of publications.

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“…The formation of 7 occurred in large part at high temperatures (Figure 2), in agreement with published results. 19 The totality of these screening results indicated a preferred temperature of 40°C for this reaction, which both preserved the diazirine and limited its participation in the competitive side reaction. Additionally, that temperature was adequate for the SPhos G2 Pd catalyst to yield an efficient cross-coupling of 2 and 5.…”

Section: Acs Medicinal Chemistry Lettersmentioning

confidence: 98%

Reducing Limitation in Probe Design: The Development of a Diazirine-Compatible Suzuki–Miyaura Cross Coupling Reaction

Ichiishi

Moore

Wassermann

et al. 2018

ACS Med. Chem. Lett.

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Access to high quality photoaffinity probe molecules is often constrained by synthetic limitations related to diazirine installation. A survey of recently published photoaffinity probe syntheses identified the Suzuki−Miyaura (S−M) coupling reaction, ubiquitous in drug discovery, as being underutilized to incorporate diazirines. To test whether advances in modern cross-coupling catalysis might enable efficient S−M couplings tolerant of the diazirine moiety, a fragment-based screening approach was employed. A model S−M coupling reaction was screened under various conditions in the presence of an aromatic diazirine fragment. This screen identified reaction conditions that gave good yields of S−M coupling product while minimally perturbing the diazirine reporter fragment. These conditions were found to be highly scalable and exhibited broad scope when applied to a chemistry informer library of 24 pharmaceutically relevant aryl boron pinacol esters. Furthermore, these conditions were used to synthesize a known diazirine-containing probe molecule with improved synthetic efficiency.

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Microwave-Assisted, Pd(0)-Catalyzed Cross-Coupling of Diazirines with Aryl Halides

Abstract: Pd(0)-catalyzed cross-coupling reactions of diazirines with aryl halides under microwave heating conditions afford a series of substituted olefins. A reaction mechanism involving the migratory insertion of the Pd carbene intermediate is proposed.

Cited by 45 publications

References 39 publications

Microwave-assisted C–C bond forming cross-coupling reactions: an overview

Microwave-assisted C–C bond forming cross-coupling reactions: an overview

New Trends in Diaziridine Formation and Transformation (a Review)

Reducing Limitation in Probe Design: The Development of a Diazirine-Compatible Suzuki–Miyaura Cross Coupling Reaction

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