A general approach to stereospecific Pd-catalyzed cross-coupling reactions of benzylic stereocenters DOI Creative Commons

Meruyert Binayeva,

Xinghua Ma,

Pejman Ghaemimohammadi

и другие.

Chemical Science, Год журнала: 2023, Номер 14(48), С. 14124 - 14130

Опубликована: Янв. 1, 2023

We have developed a general process for the formation of enantioenriched benzylic stereocenters via stereospecific Pd-catalyzed cross-coupling reactions tricyclohexyltin nucleophiles. This proceeds with excellent stereospecificity remarkably broad scope electrophilic coupling partners including aryl and heteroaryl halides triflates, acid chlorides, thioesters, chloroformates, carbamoyl chlorides. Thus, 1,1-diarylalkanes as well formal products asymmetric enolate arylation are readily accessed using this approach. additionally provide first demonstration Sn-selective reaction vicinal alkylborylstannane nucleophile. In these reactions, presence cyclohexyl spectator ligands on tin is essential to ensure selective transfer secondary unit from palladium.

Язык: Английский

Divergent Synthesis of Fluoroalkyl Ketones through Controlling the Reactivity of Organoboronate Complexes DOI
Gang Zhou,

Zhuanzhuan Guo,

Shanshan Liu

и другие.

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(6), С. 4026 - 4035

Опубликована: Фев. 1, 2024

Herein, we report a divergent synthesis of fluoroalkyl ketones through visible-light-induced reactions between readily available organoboronic esters and acylsilanes. Selective control the reactivity in situ generated organoboronate complexes is key to achieving transformations. Under basic conditions, undergo deboronative fluoride elimination, resulting formation enol silyl ethers as intermediates that react with various electrophiles generate defluorinated products. Moreover, combination peroxide, 1,2-shift group favored over elimination ketal intermediates, leading This transition-metal-free reaction operationally simple, aryl, alkenyl, alkyl boronic are all suitable substrates. The synthetic potential has been demonstrated by gram-scale facile bioactive molecules including zifrosilone its analogs.

Язык: Английский

Процитировано

29

Silyl Radical Generation from Silylboronic Pinacol Esters through Substitution with Aminyl Radicals DOI

Hongyan Lan,

Xiangyu Huo,

Ying‐Gang Jia

и другие.

Organic Letters, Год журнала: 2024, Номер 26(5), С. 1011 - 1016

Опубликована: Янв. 30, 2024

A novel strategy was developed to generate silyl radicals from silylboronic pinacol esters (SPEs) through nucleohomolytic substitution of boron with aminyl radicals. We successfully applied this obtain diverse organosilicon compounds using SPEs and N-nitrosamines under photoirradiation without any catalyst. The ability access offers a new perspective for chemists rapidly construct Si–X bonds.

Язык: Английский

Процитировано

11

Photo-mediated radical relay oximinosulfonamidation of alkenes with N-nitrosamines triggered by DABSO DOI

Ji‐Wei Sang,

Hong Chen, Yu Zhang

и другие.

Green Chemistry, Год журнала: 2024, Номер 26(13), С. 7849 - 7856

Опубликована: Янв. 1, 2024

N -Nitrosamines represent a class of bifunctional nitrogen-radical precursors, but their application potential remains largely unexplored.

Язык: Английский

Процитировано

7

Emerging progress: photochemical transformation of nitroso compounds DOI

Ze‐Le Chen,

Qiangqiang Li, Armido Studer

и другие.

Science China Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Июль 17, 2024

Язык: Английский

Процитировано

7

Deboronative functionalization of alkylboron species via a radical-transfer strategy DOI Creative Commons

Fuyang Yue,

Mingxing Li, Kangkang Yang

и другие.

Chemical Science, Год журнала: 2024, Номер 15(35), С. 14241 - 14247

Опубликована: Янв. 1, 2024

We describe a method for activating C–B bonds by nitrogen- or oxygen-radical transfer that is applicable to alkylboronic acids and esters.

Язык: Английский

Процитировано

6

Cu‐Catalyzed Coupling of Aliphatic Amines with Alkylboronic Esters DOI Creative Commons
Francesca M. Dennis, Antonio Romero‐Arenas, George Rodgers

и другие.

Chemistry - A European Journal, Год журнала: 2024, Номер 30(19)

Опубликована: Янв. 3, 2024

Abstract We report a Cu‐catalyzed oxidative coupling of aliphatic amines with benzylic and boronic esters to give high value alkyl amines, products found widely in applications from medicinal chemistry materials science. This operationally simple reaction, which can be performed on gram scale, runs under mild conditions exhibits broad functional group tolerance. The terminal oxidant the reaction is O 2 air, avoiding need for additional chemical oxidants. Investigation into mechanism suggests that ester activated by an aminyl radical, formed through oxidation amine Cu catalyst, key radical intermediate. To demonstrate its utility potential late‐stage functionalization, we showcase method as final step total synthesis TRPV1 antagonist.

Язык: Английский

Процитировано

5

Light‐Induced Domino and Multicomponent Reactions: How to Reach Molecular Complexity without a Catalyst DOI Creative Commons
Polyssena Renzi, Jacopo Scarfiello, Alberto Lanfranco

и другие.

European Journal of Organic Chemistry, Год журнала: 2023, Номер unknown

Опубликована: Авг. 31, 2023

Abstract Achieving high molecular complexity can be not trivial, but the exploitation of domino reactions provides an atom‐ and step‐economical method to reach this target. Over past decades, a lot efforts have been put on development photocatalytic cascades employing both metal‐based purely organic catalysts. Despite effectiveness these protocols, catalyst‐ additive‐free light‐induced are gaining momentum thank their efficiency, operational simplicity sustainability. The increasing number papers published field in last years is proof appeal transformations. In Review, we discuss multicomponent mediated by light with focus photocatalyst‐ processes. most recent advances synthesis complex nitrogen‐, oxygen‐, sulphur‐ selenium‐heterocycles together analysed emphasis experimental mechanistic studies.

Язык: Английский

Процитировано

10

Visible-Light-Driven Iron-Catalyzed Decarboxylative C–N Coupling Reaction of Alkyl Carboxylic Acids with NaNO2 DOI
Shilei Yang, Yi Wang,

XU Wen-yao

и другие.

Organic Letters, Год журнала: 2023, Номер 25(49), С. 8834 - 8838

Опубликована: Дек. 6, 2023

An efficient visible-light-driven iron-catalyzed decarboxylative C-N coupling reaction of alkyl carboxylic acids with NaNO2 under mild conditions was developed. The proceeds photosensitizer-free and features good to excellent yields, broad functional group tolerance, an easy operation procedure. Preliminary mechanistic investigations showed that iron catalysis not only achieved oxidative decarboxylation radicals but also promoted the reduction NO2- NO, thus leading radical reaction.

Язык: Английский

Процитировано

10

A general photochemical strategy for the oximation of activated alkenes without a catalyst DOI

Hongyan Lan,

You Su,

Y. Chen

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(15), С. 4207 - 4213

Опубликована: Янв. 1, 2024

A general photochemical approach for the oximation of activated alkenes to synthesize diverse oximes without catalysts is described. The simple and modular method offers a new perspective chemists rapidly obtain various radical intermediates.

Язык: Английский

Процитировано

3

Visible-light-induced photocatalyst- and metal-free radical phosphinoyloximation of alkenes with tert-butyl nitrite as bifunctional reagent DOI
Huihui Yang, Miaomiao Li, Aijun Zhang

и другие.

Chinese Chemical Letters, Год журнала: 2024, Номер unknown, С. 110425 - 110425

Опубликована: Окт. 1, 2024

Язык: Английский

Процитировано

3