Divergent gold-catalysed reactions of cyclopropenylmethyl sulfonamides with tethered heteroaromatics

Drew, Melanie A.; Arndt, Sebastian; Richardson, Christopher; Rudolph, Matthias; Hashmi, A. Stephen K.; Hyland, Christopher J. T.

doi:10.1039/c9cc06241f

Cited by 17 publications

(10 citation statements)

References 65 publications

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“…30 Gratifyingly, the N-Ts group could be readily removed from 2a upon sonication in the presence of Mg/MeOH to produce 1-methyl-5-phenylisoindoline 5 in excellent yieldit should be noted, however, that this product is unstable and cannot be puried by chromatography. 31…”

Section: Resultsmentioning

confidence: 99%

Rhodium-catalysed tetradehydro-Diels–Alder reactions of enediynes via a rhodium-stabilized cyclic allene

et al. 2020

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Section: Resultsmentioning

confidence: 99%

Rhodium-catalysed tetradehydro-Diels–Alder reactions of enediynes via a rhodium-stabilized cyclic allene

et al. 2020

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“…A related strategy was employed by Hashmi et al to generate interesting heterocyclic scaffolds. In this case, cyclopropene derivatives 79 bearing a tethered heteroaromatic ring on the Csp 3 center of the strained ring were used ( Scheme 11 ) [ 60 ]. The outcome of the cyclization reaction was heavily dependent on the type of heterocycle present in the substrate.…”

Section: Synthetic Methodology Involving C–h Functionalization Alomentioning

confidence: 99%

Recent Advances on Synthetic Methodology Merging C–H Functionalization and C–C Cleavage

Azizollahi

Garcı́a-López

2020

Molecules

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The functionalization of C–H bonds has become a major thread of research in organic synthesis that can be assessed from different angles, for instance depending on the type of catalyst employed or the overall transformation that is carried out. This review compiles recent progress in synthetic methodology that merges the functionalization of C–H bonds along with the cleavage of C–C bonds, either in intra- or intermolecular fashion. The manuscript is organized in two main sections according to the type of substrate in which the cleavage of the C–C bond takes place, basically attending to the scission of strained or unstrained C–C bonds. Furthermore, the related research works have been grouped on the basis of the mechanistic aspects of the different transformations that are carried out, i.e.,: (a) classic transition metal catalysis where organometallic intermediates are involved; (b) processes occurring via radical intermediates generated through the use of radical initiators or photochemically; and (c) reactions that are catalyzed or mediated by suitable Lewis or Brønsted acid or bases, where molecular rearrangements take place. Thus, throughout the review a wide range of synthetic approaches show that the combination of C–H and C–C cleavage in single synthetic operations can serve as a platform to achieve complex molecular skeletons in a straightforward manner, among them interesting carbo- and heterocyclic scaffolds.

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“…Shortly after, Hyland and co-workers reported the goldcatalyzed cyclizations of cyclopropenes 215 decorated in remote positions with heteroarenes connected by C2-atom (Scheme 33C). 161 For indole-or pyrrol-containing reagents 215, the reaction led to the formation of carboline derivatives 216 in good yields, albeit the scope shown was somewhat restricted. The formation of these compounds could be explained by a gold-promoted cyclopropene opening to an allyl-gold cation intermediate, which was then trapped via S E Ar-type reaction by the heteroarene through the C3 atom leading to a vinyl gold species.…”

Section: Electrophilic Aromatic Substitution Reactions Using Cyclopro...mentioning

confidence: 99%

“…Shortly after, Hyland and co-workers reported the gold-catalyzed cyclizations of cyclopropenes 215 decorated in remote positions with heteroarenes connected by C2-atom (Scheme C) . For indole- or pyrrol-containing reagents 215 , the reaction led to the formation of carboline derivatives 216 in good yields, albeit the scope shown was somewhat restricted.…”

Section: Electrophilic Aromatic Substitution Reactions Using Cyclopro...mentioning

confidence: 99%

C–C Bond Cleavages of Cyclopropenes: Operating for Selective Ring-Opening Reactions

Vicente

2020

Chem. Rev.

117

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This review highlights key reactivities relying on C–C bond cleavages of cyclopropenes. Metal-catalyzed and metal-free transformations are covered in reactions involving direct ring-opening processes or transformations through nonisolable cyclopropane intermediates generated from cyclopropenes. Special emphasis is on the synthetic utility and mechanistic aspects of methodologies discussed along the revision. Different types of reactivities are covered in separate sections including generation of vinyl carbenes and their reactions, metathesis processes, heterocycles syntheses, SEAr reactions, metalation-ring opening sequences, cycloadditions involving ring-cleavages or rearrangements. The focus is on results described from 2007 to the end of 2019, yet relevant pioneering transformations are eventually included.

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Divergent gold-catalysed reactions of cyclopropenylmethyl sulfonamides with tethered heteroaromatics

Abstract: Cyclopropenylmethyl sulfonamides with tethered heteroaromatics can undergo divergent gold-catalysed cyclisation reactions based on the nature of the aromatic tether.

Cited by 17 publications

References 65 publications

Rhodium-catalysed tetradehydro-Diels–Alder reactions of enediynes via a rhodium-stabilized cyclic allene

Rhodium-catalysed tetradehydro-Diels–Alder reactions of enediynes via a rhodium-stabilized cyclic allene

Recent Advances on Synthetic Methodology Merging C–H Functionalization and C–C Cleavage

C–C Bond Cleavages of Cyclopropenes: Operating for Selective Ring-Opening Reactions

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