Organocatalytic C(sp<sup>3</sup>)–H Functionalization of 5-Methyl-2,3-dihydrofuran Derivatives with Trifluoropyruvates via a Sequential <i>exo</i>-Tautomerization/Carbonyl-Ene Process

Shen, Yao‐Bin; Li, Shuaishuai; Sun, Yun-Ming; Yu, Liping; Hao, Zhihui; Liu, Qing; Xiao, Jian

doi:10.1021/acs.joc.8b03170

Cited by 10 publications

References 58 publications

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Organocatalytic Routes to CH Functionalization Reactions

Barik¹,

Biju²

2022

Handbook of CH-Functionalization

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Transition metal‐catalyzed reactions are powerful and routinely used for the functionalization of inert CH bonds. However, the toxicity of the metals, cost of the metal catalysts, and their availability limit the potential application of this strategy. Organocatalysis is an elegant alternative, and in few cases, provides reaction outcomes unparalleled in transition metal catalysis. The use of various organocatalytic techniques such as secondary amine catalysis, N ‐heterocyclic carbene catalysis, H‐bonding catalysis, photoredox catalysis, etc. can be utilized for the transition metal‐free CH functionalization reactions. This article is aimed at highlighting the organocatalytic protocols for inert CH functionalization reactions (with selected examples) giving special emphasis on the catalytic mode of action and the type of inert CH bond being functionalized.

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Organocatalytic Routes to CH Functionalization Reactions

Barik¹,

Biju²

2022

Handbook of CH-Functionalization

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Chemodivergent Photocatalytic Synthesis of Dihydrofurans and β,γ‐Unsaturated Ketones

et al. 2021

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A synthetic procedure, catalysed by Ir(ppy)3 under visible‐light irradiation, for the chemodivergent synthesis of 2,3‐dihydrofurans (3) or β,γ‐unsaturated ketones (7) starting from α‐halo ketones (1) and alkenes (2) has been developed. The mild reaction conditions and the redox‐neutral nature of the process make it particularly sustainable avoiding the use of both sacrificial reactants and stoichiometric strong oxidants. Careful experimental investigations, supported by DFT calculations, allowed to disclose in details a possible mechanistic pathway and to direct the synthesis chemodivergently either toward 3 or 7, depending not only on the nature of the substrates, but also on the choice of the experimental conditions.

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Enantioselective Synthesis of Spiro Chroman‐Isoindolinones via Formal (4+2) Cycloaddition of In Situ‐Generated ortho‐Quinone Methides with 3‐Methylene Isoindolinones

2022

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Using chiral phosphoric acids as organocatalysts, a formal asymmetric (4+2) cycloaddition of 3‐methylene isoindolinone and in situ‐generated ortho‐quinone methide substrates is disclosed. This reaction exhibited a broad substrate scope with various substituted cyclic enamides and ortho‐hydroxybenzyl alcohol derivatives to construct a series of spiro chroman‐isoindolinones containing spiro‐N,O‐heterocycles with 56 to 93% ee. This strategy demonstrates significant potential towards establishing a chiral spiro‐N,O‐aminal systems bearing two chiral carbon centers, including a tetrasubstituted carbon stereocenter.

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Organocatalytic C(sp³)–H Functionalization of 5-Methyl-2,3-dihydrofuran Derivatives with Trifluoropyruvates via a Sequential exo-Tautomerization/Carbonyl-Ene Process

Cited by 10 publications

References 58 publications

Organocatalytic Routes to CH Functionalization Reactions

Organocatalytic Routes to CH Functionalization Reactions

Chemodivergent Photocatalytic Synthesis of Dihydrofurans and β,γ‐Unsaturated Ketones

Enantioselective Synthesis of Spiro Chroman‐Isoindolinones via Formal (4+2) Cycloaddition of In Situ‐Generated ortho‐Quinone Methides with 3‐Methylene Isoindolinones

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Organocatalytic C(sp3)–H Functionalization of 5-Methyl-2,3-dihydrofuran Derivatives with Trifluoropyruvates via a Sequential exo-Tautomerization/Carbonyl-Ene Process

Cited by 10 publications

References 58 publications

Organocatalytic Routes to CH Functionalization Reactions

Organocatalytic Routes to CH Functionalization Reactions

Chemodivergent Photocatalytic Synthesis of Dihydrofurans and β,γ‐Unsaturated Ketones

Enantioselective Synthesis of Spiro Chroman‐Isoindolinones via Formal (4+2) Cycloaddition of In Situ‐Generated ortho‐Quinone Methides with 3‐Methylene Isoindolinones

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Organocatalytic C(sp³)–H Functionalization of 5-Methyl-2,3-dihydrofuran Derivatives with Trifluoropyruvates via a Sequential exo-Tautomerization/Carbonyl-Ene Process