Hydrogenative alkene perdeuteration aided by a transient cooperative ligand

Nature Chemistry, Journal Year: 2023, Volume and Issue: 15(10), P. 1384 - 1390

Published: Sept. 4, 2023

Language: Английский

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Electroreductively Induced Radicals for Organic Synthesis

Molecules, Journal Year: 2023, Volume and Issue: 28(2), P. 857 - 857

Published: Jan. 15, 2023

Organic electrochemistry has attracted tremendous interest within the novel sustainable methodologies that have not only reduced undesired byproducts, but also utilized cleaner and renewable energy sources. Particularly, oxidative gained major attention. On contrary, reductive electrolysis remains an underexplored research direction. In this context, we discuss advances in transition-metal-free cathodically generated radicals for selective organic transformations since 2016. We highlight electroreductive reaction of alkyl radicals, aryl acyl silyl fluorosulfonyl trifluoromethoxyl radicals.

Language: Английский

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Chemoselective 1,2‐Reduction and Regiodivergent Deuteration of Chromium‐Bound Arenes

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(18)

Published: Feb. 23, 2023

Herein, a general strategy for chemo- and regioselective 1,2-reduction of chromium-bound arenes was developed, thus providing rapid access to 1,3-cyclohexadienes. Selective arene activation via π-complexation along with the use mild hydride Ph3 SiH can overcome inherently low reactivity π-bonds while tolerating various reduction-sensitive functional groups. Its versatility further enables regiodivergent deuteration. Using different sequences (non)deuterated acid reagents, deuterated positions as well degrees deuterium incorporation be controlled precisely, which leads large previously inaccessible chemical space 1,3-cyclohexadiene isotopologues. A reasonable mechanism proposed based on intermediate capture control experiments. The synthetic value this selective demonstrated in formal total synthesis (±)-galanthamine (±)-lycoramine.

Language: Английский

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A General Organophotoredox Strategy to Difluoroalkyl Bicycloalkane (CF2‐BCA) Hybrid Bioisosteres**

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(31)

Published: June 1, 2023

Here, we report a general approach to the synthesis of difluoroalkyl bicycloalkanes (CF2 -BCAs), as structural surrogates aryl ketones and ethers. The chemistry is driven by dihydrobenzoacridine photocatalyst, that engages in catalytic electron-donor acceptor (EDA) complex, or directly reduces fluorinated substrate. These two convergent manifolds lead generation R-CF2 radical, reacts with [1.1.1]- [3.1.1.]-propellane. method extremely general, extendable complex bioactive molecules (30 examples, up 87 % yield). features CF2 -BCP hybrid bioisostere were investigated single crystal X-ray. Finally, synthesised analogue Leukotriene A4 hydrolase inhibitor, replacing original ether motif. In silico docking studies indicated this new maintains same arrangement within enzyme pocket, profiling use -BCA medicinal settings.

Language: Английский

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Electrochemical C−H deuteration of pyridine derivatives with D2O

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: May 7, 2024

Herein, we develop a straightforward, metal-free, and acid-/base-free electrochemical C4-selective C - H deuteration of pyridine derivatives with economic convenient D

Language: Английский

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