Rhodium(III)-catalyzed C–H functionalization of C-alkenyl azoles with sulfoxonium ylides for the synthesis of bridgehead N-fused [5,6]-bicyclic heterocycles

Hoang, Gia L.; Ellman, Jonathan A.

doi:10.1016/j.tet.2018.03.062

Cited by 42 publications

(12 citation statements)

References 34 publications

(14 reference statements)

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“…Ellman et al extended their study to activate alkenyl C-H for the synthesis of other N-fused [5,6]-bicyclic heterocycles (Scheme 35). 54 In this study, 2-alkenyl imidazoles and triazoles 80 reacted with sulfoxonium ylide derived rhodium carbenoids via rhodacycle 82 to annulated heterocycles 81. Remarkably, the reaction was carried out under benchtop conditions at 2 mmol scale for aryl and alkyl sulfoxonium ylides without anhydrous reaction conditions.…”

Section: Scheme 34 Rh(iii)-catalyzed Imidoyl C-h Activation and Annulmentioning

confidence: 92%

Sulfoxonium Ylide Derived Metal Carbenoids in Organic Synthesis

Vaitla

Bayer

2018

Synthesis

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As pioneered by Corey and Chaykovsky, sulfoxonium ylides have had widespread application in organic synthesis for more than a half century. In most of the reactions, sulfoxonium ylides were used to react with electrophiles. Under suitable reaction conditions these ylides can generate metal carbenoids and react with nucleophiles. By combining the typical reactivity of sulfoxonium ylides with transition-metal catalysis, a growing number of investigations have expanded their application in organic synthesis. This review provides an update on the preparation of sulfoxonium ylides and their applications in carbenoid transfer reactions.1 Introduction2 Preparation of Sulfoxonium Ylides3 Investigation for Carbenoid Formation from Sulfoxonium Ylide 4 X–H (X = N, O, S, C) Functionalization Reactions5 Polymerizaton of Carbenoids Generated from Sulfoxonium Ylides6 Conclusion and Perspective

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Section: Scheme 34 Rh(iii)-catalyzed Imidoyl C-h Activation and Annulmentioning

confidence: 92%

Sulfoxonium Ylide Derived Metal Carbenoids in Organic Synthesis

Vaitla

Bayer

2018

Synthesis

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“…Since these contributions, this type of ylide has been employed in several important and new transformations that explore its ambiphilic behavior. Formation of C–C, C–N, C–O, and C–halogen bonds, synthesis of naphthols, indoles, and pyrroles, cross-coupling reactions, , and synthesis of difunctionalized haloketones, among others, − are some of the very recent examples (Figure ).…”

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confidence: 99%

Coupling of Sulfoxonium Ylides with Arynes: A Direct Synthesis of Pro-Chiral Aryl Ketosulfoxonium Ylides and Its Application in the Preparation of α-Aryl Ketones

2018

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A general, mild, and versatile synthesis of the challenging α-aryl-β-ketosulfoxonium ylides has been developed for the first time, substituting traditional methods starting from diazo compounds. The arylation of easily accessible βketosulfoxonium ylides using aryne chemistry allowed the preparation of a large scope of the pro-chiral ylides in very good yields (40 examples; up to 85%). As applications, these ylides were smoothly converted into α-aryl ketones after desulfurization in good yields (up to 98%) as well as in other important derivatives.Letter pubs.acs.org/OrgLett

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“…However, transition-metal-catalyzed C–H insertion reactions of sulfoxonium ylides are rarely studied. Only very recently, Aı̈ssa, Li, and others reported the Cp*Rh(III)-catalyzed C–H functionalization of arenes with sulfoxonium ylides as carbene precursors and coupling partners (Scheme b) …”

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confidence: 99%