Photoinduced Remote Functionalisations by Iminyl Radical Promoted C−C and C−H Bond Cleavage Cascades DOI Creative Commons
Elizabeth M. Dauncey, Sara P. Morcillo, James J. Douglas

и другие.

Angewandte Chemie, Год журнала: 2017, Номер 130(3), С. 752 - 756

Опубликована: Ноя. 8, 2017

Abstract A photoinduced cascade strategy leading to a variety of differentially functionalised nitriles and ketones has been developed. These reactions rely on the oxidative generation iminyl radicals from simple oximes. Radical transposition by C(sp 3 )−(sp ) )−H bond cleavage gives access distal carbon that undergo S H 2 functionalisations. mild, visible‐light‐mediated procedures can be used for remote fluorination, chlorination, azidation, were applied modification bioactive structurally complex molecules.

Язык: Английский

Iron-Catalyzed Decarboxylative Olefination of Cycloketone Oxime Esters with α,β-Unsaturated Carboxylic Acids via C–C Bond Cleavage DOI

Jing‐Feng Zhao,

Xin‐Hua Duan,

Yu‐Rui Gu

и другие.

Organic Letters, Год журнала: 2018, Номер 20(15), С. 4614 - 4617

Опубликована: Июль 19, 2018

An iron-catalyzed redox-neutral, decarboxylative olefination of cycloketone oxime esters with α,β-unsaturated carboxylic acids has been developed. This reaction involves an iminyl radical mediated C–C bond cleavage/radical addition/decarboxylation cascade. protocol is highlighted by its low-cost catalytic system and readily accessible starting materials, as well broad substrate scope, thus providing facile access to structurally diverse cyano-containing alkenes.

Язык: Английский

Процитировано

106

Synthesis of gem-Difluoroalkenes by Merging Ni-Catalyzed C–F and C–C Bond Activation in Cross-Electrophile Coupling DOI

Decai Ding,

Yun Lan, Zhiyang Lin

и другие.

Organic Letters, Год журнала: 2019, Номер 21(8), С. 2723 - 2730

Опубликована: Март 29, 2019

By merging C–F and C–C bond activation in the cross-electrophile coupling, we developed an efficient cyanide-free synthesis of diverse functional-group-rich cyano-substituted gem-difluoroalkenes using cyclobutanone oxime esters trifluoromethyl alkenes as precursors. Notably, this Ni-catalyzed reaction is bestowed with broad substrate scope, low catalyst loading, complete regioselectivities, high tolerance a wide range sensitive functional groups. Preliminary mechanistic studies indicate that iminyl radical-initiated cleavage involved pathway.

Язык: Английский

Процитировано

106

Copper-Catalyzed Redox-Neutral Cyanoalkylarylation of Activated Alkenes with Cyclobutanone Oxime Esters DOI
Jun Wu, Jiayu Zhang, Pin Gao

и другие.

The Journal of Organic Chemistry, Год журнала: 2017, Номер 83(2), С. 1046 - 1055

Опубликована: Дек. 14, 2017

The copper-catalyzed cyclization of activated alkenes with cyclobutanone O-acyl oximes under redox-neutral conditions has been reported. This facile protocol provided an efficient approach to a variety cyanoalkylated oxindoles and dihydroquinolin-2(1H)-ones broad substrate scope excellent functional group tolerance. In this reaction, sequential C–C bond cleavage, radical addition, processes were involved, wherein multiple bonds constructed in one-pot reaction. Mechanistic studies suggest that the reaction probably proceeded via pathway.

Язык: Английский

Процитировано

103

Recent advances in cyclization reactions of unsaturated oxime esters (ethers): synthesis of versatile functionalized nitrogen-containing scaffolds DOI
Chen Chen, Jinghui Zhao, Xiaonan Shi

и другие.

Organic Chemistry Frontiers, Год журнала: 2020, Номер 7(14), С. 1948 - 1969

Опубликована: Янв. 1, 2020

We summarized recent advances in cyclization reactions of unsaturated oxime esters (ethers), which provide diversiform functionalized nitrogen-containing scaffolds.

Язык: Английский

Процитировано

96

Photoinduced Remote Functionalisations by Iminyl Radical Promoted C−C and C−H Bond Cleavage Cascades DOI Creative Commons
Elizabeth M. Dauncey, Sara P. Morcillo, James J. Douglas

и другие.

Angewandte Chemie, Год журнала: 2017, Номер 130(3), С. 752 - 756

Опубликована: Ноя. 8, 2017

Abstract A photoinduced cascade strategy leading to a variety of differentially functionalised nitriles and ketones has been developed. These reactions rely on the oxidative generation iminyl radicals from simple oximes. Radical transposition by C(sp 3 )−(sp ) )−H bond cleavage gives access distal carbon that undergo S H 2 functionalisations. mild, visible‐light‐mediated procedures can be used for remote fluorination, chlorination, azidation, were applied modification bioactive structurally complex molecules.

Язык: Английский

Процитировано

96