Ligand‐Controlled Direct γ‐C−H Arylation of Aldehydes

Li, Bijin; Lawrence, Brianna; Li, Guigen; Ge, Haibo

doi:10.1002/ange.201913126

Cited by 18 publications

(2 citation statements)

References 59 publications

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“…Additionally, this TDG needs to be chemo-orthogonal to the catalytic reaction of interest, such that neither catalytic cycle is inhibited or perturbed to instead form undesired side products. The viability of catalytic TDGs has previously been established in several mechanistically distinct transitionmetal-catalyzed reactions, including in the field of CÀH activation; [11] however, there are comparatively few examples of efficient chiral TDGs in metal catalysis, and the scope of these transformations remains limited. Early examples by the groups of Bergman/Ellman [12a] and Douglas [12b] focused on intramolecular alkene cyclizations, but achieved only modest enantioinduction (Scheme 1 B, left).…”

mentioning

confidence: 99%

A Transient‐Directing‐Group Strategy Enables Enantioselective Reductive Heck Hydroarylation of Alkenes

Oxtoby

Erbay

et al. 2020

Angewandte Chemie

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Metal‐coordinating directing groups have seen extensive use in the field of transition‐metal‐catalyzed alkene functionalization; however, their waste‐generating installation and removal steps limit the efficiency and practicality of reactions that rely on their use. Inspired by developments in asymmetric organocatalysis, where reactions rely on reversible covalent interactions between an organic substrate and a chiral mediator, we have developed a transient‐directing‐group approach to reductive Heck hydroarylation of alkenyl benzaldehyde substrates that proceeds under mild conditions. Highly stereoselective migratory insertion is facilitated by in situ formation of an imine from catalytic amounts of a commercially available amino acid additive. Computational studies reveal an unusual mode of enantioinduction by the remote chiral center in the transient directing group.

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mentioning

confidence: 99%

A Transient‐Directing‐Group Strategy Enables Enantioselective Reductive Heck Hydroarylation of Alkenes

Oxtoby

Erbay

et al. 2020

Angewandte Chemie

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“…arylation of 3-methylbenzothiophene-2-carbaldehyde/3-methylbenzofuran-2-carbaldehyde with iodobenzene was performed (Scheme 21). 39 Then, the direct use of 3-benzylbenzothiophene-2-carbaldehyde and 3-benzylbenzofuran-2-carbaldehyde as starting materials to react with TPA-bearing 2-(4-(oxazol-2-yl)phenyl)acetonitrile produced novel organic functional molecules 38 (Scheme 22; Figure 10). The luminous properties of 38a and 38b were investigated with respect to emission maxima in toluene solution and before and after grinding (Figure 10).…”

Section: Transition-metal-catalyzed C-h Functionalization To Build Fluorescent Materialsmentioning

confidence: 99%

Recent Advances in Using Transition-Metal-Catalyzed C–H Functionalization to Build Fluorescent Materials

Ali

2020

Chem

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108

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Organic fluorescent molecules have broad applications in modern technology, such as in security systems, chemosensors, bioprobes, field-effect transistors, memory devices, organic light-emitting diodes, etc. The transition-metal-catalyzed C-H bond functionalization approach represents a distinct, facile, and atom-efficient tactic for the construction of organic fluorescent molecules, which are often difficult to prepare using typical synthetic methods. In this review, four types of C-H bond functionalization reactions for the preparation of fluorescent materials are discussed: (1) transition-metal-catalyzed C-H/C-X cross-coupling reactions; (2) transition-metal-catalyzed C-H/C-H cross-coupling reactions; (3) transitionmetal-catalyzed C-H addition and/or annulation reactions; and (4) transition-metal-catalyzed C-H/C-M or C-H/Het-H bond functionalization. The objective of this review is to characterize the current state of the art in using transition-metal-catalyzed C-H functionalization to build fluorescent molecules as well as their application in electroluminescent materials, mechanofluorochromic materials, labels, sensors for bioimaging, etc.

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Divergent Auto‐oxidative Alkylation and Alkanoacylation of Quinoxalin‐2(1H)‐ones with Aliphatic Aldehydes

Shen

et al. 2022

Asian J Org Chem

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Auto-oxidation of aliphatic aldehydes generates alkyl radicals and alkanoyl radicals, which can be intercepted to generate carbon-carbon bonds. However, the highly reactive and unstable radical intermediates make the controlling selectivity alkylation and alkanoacylation especially challenging. Herein, we report a sustainable and controllable protocol for the auto-oxidative alkylation and alkanoacylation of quinoxalin-2(1H)-ones with good reactivity and selectivity. This protocol was presented in a green and sustainable manner, using oxygen as the only oxidant, avoiding the use of catalysts and explosive oxidants. It offers a new paradigm for a convenient, green synthesis of alkyl and alkanoyl compounds from abundant aliphatic aldehydes.

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Ligand‐Controlled Direct γ‐C−H Arylation of Aldehydes

Cited by 18 publications

References 59 publications

A Transient‐Directing‐Group Strategy Enables Enantioselective Reductive Heck Hydroarylation of Alkenes

A Transient‐Directing‐Group Strategy Enables Enantioselective Reductive Heck Hydroarylation of Alkenes

Recent Advances in Using Transition-Metal-Catalyzed C–H Functionalization to Build Fluorescent Materials

Divergent Auto‐oxidative Alkylation and Alkanoacylation of Quinoxalin‐2(1H)‐ones with Aliphatic Aldehydes

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