Rhodium(III)-Catalyzed Synthesis of Naphthols via C–H Activation of Sulfoxonium Ylides

Xu, Youwei; Yang, Xifa; Zhou, Xukai; Kong, Lingheng; Li, Xingwei

doi:10.1021/acs.orglett.7b01974

Cited by 140 publications

(62 citation statements)

References 42 publications

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“…In conclusion, the cross-coupling described herein expands the traditional chemistry of sulfoxonium ylides [20] and brings these reagents into the realm of metal-catalyzed C À Ha ctivation. [21,22]…”

Section: Angewandte Chemiementioning

confidence: 99%

Cross‐Coupling of α‐Carbonyl Sulfoxonium Ylides with C−H Bonds

et al. 2017

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The functionalization of carbon-hydrogen bonds in non-nucleophilic substrates using α-carbonyl sulfoxonium ylides has not been so far investigated, despite the potential safety advantages that such reagents would provide over either diazo compounds or their in situ precursors. Described herein are the cross-coupling reactions of sulfoxonium ylides with C(sp )-H bonds of arenes and heteroarenes in the presence of a rhodium catalyst. The reaction proceeds by a succession of C-H activation, migratory insertion of the ylide into the carbon-metal bond, and protodemetalation, the last step being turnover-limiting. The method is applied to the synthesis of benz[c]acridines when allied to an iridium-catalyzed dehydrative cyclization.

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Section: Angewandte Chemiementioning

confidence: 99%

Cross‐Coupling of α‐Carbonyl Sulfoxonium Ylides with C−H Bonds

et al. 2017

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“…In conclusion, the cross‐coupling described herein expands the traditional chemistry of sulfoxonium ylides and brings these reagents into the realm of metal‐catalyzed C−H activation …”

Section: Figurementioning

confidence: 89%

Cross‐Coupling of α‐Carbonyl Sulfoxonium Ylides with C−H Bonds

et al. 2017

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The functionalization of carbon–hydrogen bonds in non‐nucleophilic substrates using α‐carbonyl sulfoxonium ylides has not been so far investigated, despite the potential safety advantages that such reagents would provide over either diazo compounds or their in situ precursors. Described herein are the cross‐coupling reactions of sulfoxonium ylides with C(sp2)−H bonds of arenes and heteroarenes in the presence of a rhodium catalyst. The reaction proceeds by a succession of C−H activation, migratory insertion of the ylide into the carbon–metal bond, and protodemetalation, the last step being turnover‐limiting. The method is applied to the synthesis of benz[c]acridines when allied to an iridium‐catalyzed dehydrative cyclization.

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“…The year 2017 saw the publication of three papers on the subject, two by the laboratory of Li, and one by the laboratory of Aïssa. The first of these papers focussed on the use of stabilised sulfoxonium ylides ( 18 ) able to direct C–H activation [ 37 ]. By combining benzoyl sulfoxonium ylides with alkynes under the action of Rh(III) catalysis, Li and co-workers were able to synthesise a range of naphthol derivatives ( 19 ) in mostly excellent yields (Scheme 16 ).…”

Section: Non-carbene-based Transition Metal-mediated Reactions Of Sulmentioning

confidence: 99%

Sulfur-Based Ylides in Transition-Metal-Catalysed Processes

et al. 2018

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Traditionally employed in the synthesis of small ring systems and rearrangement chemistry, sulfur-based ylides occupy a unique position in the toolbox of the synthetic organic chemist. In recent years a number of pioneering researchers have looked to expand the application of these unorthodox reagents through the use of transition metal catalysis. The strength and flexibility of such a combination have been shown to be of key importance in developing powerful novel methodologies. This chapter summarises recent developments in transition metal-catalysed sulfonium/sulfoxonium ylide reactions, as well as providing a historical perspective. In overviewing the successes in this area, the authors hope to encourage others into this growing field.

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Rhodium(III)-Catalyzed Synthesis of Naphthols via C–H Activation of Sulfoxonium Ylides

Cited by 140 publications

References 42 publications

Cross‐Coupling of α‐Carbonyl Sulfoxonium Ylides with C−H Bonds

Cross‐Coupling of α‐Carbonyl Sulfoxonium Ylides with C−H Bonds

Cross‐Coupling of α‐Carbonyl Sulfoxonium Ylides with C−H Bonds

Sulfur-Based Ylides in Transition-Metal-Catalysed Processes

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