Metal-Free One-Pot Multi-Functionalization of Unsaturated Compounds with Interelement Compounds by Radical Process DOI Creative Commons
Yuki Yamamoto, Akiya Ogawa

Molecules, Год журнала: 2023, Номер 28(2), С. 787 - 787

Опубликована: Янв. 12, 2023

In recent years, the importance of “environmentally friendly manufacturing” has been increasing toward establishment a resource-recycling society. organic synthesis, as well, it is becoming increasingly important to develop new synthetic strategies with resource conservation and recycling elemental resources in mind, rather than just only synthesis. Many studies on construction frameworks functional molecules using ionic reactions transition-metal-catalyzed have reported, but most them focused formation carbon–carbon bonds. However, essential introduce appropriate groups at positions order for express their functions, furthermore, highly selective preparation multiple considered creation molecules. this review, we focus radical high group selectivity overview progress practical methods simultaneous introduction propose future that emphasize environmental friendliness.

Язык: Английский

Radical-mediated rearrangements: past, present, and future DOI
Xinxin Wu, Zhigang Ma, Tingting Feng

и другие.

Chemical Society Reviews, Год журнала: 2021, Номер 50(20), С. 11577 - 11613

Опубликована: Янв. 1, 2021

This Review summarizes the past to present achievements in radical-mediated rearrangements, and brings up prospects that may inspire colleagues develop more useful synthetic tools based on radical rearrangements.

Язык: Английский

Процитировано

214
Cooperative NHC and Photoredox Catalysis for the Synthesis of β‐Trifluoromethylated Alkyl Aryl Ketones DOI Creative Commons
Qingyuan Meng,

Nadine Döben,

Armido Studer

и другие.

Angewandte Chemie International Edition, Год журнала: 2020, Номер 59(45), С. 19956 - 19960

Опубликована: Июль 23, 2020

Despite the great potential of radical chemistry in organic synthesis, N-heterocyclic carbene (NHC)-catalyzed reactions involving intermediates are not well explored. This communication reports three-component coupling aroyl fluorides, styrenes and Langlois reagent (CF3 SO2 Na) to give various β-trifluoromethylated alkyl aryl ketones with good functional group tolerance moderate high yields by cooperative photoredox/NHC catalysis. The alkene acyltrifluoromethylation proceeds via radical/radical cross ketyl radicals benzylic C-radicals. generated SET reduction situ formed acylazolium ions whereas derive from trifluoromethyl addition onto styrenes.

Язык: Английский

Процитировано

202
Photocatalytic C(sp3) radical generationviaC–H, C–C, and C–X bond cleavage DOI Creative Commons
Chia‐Yu Huang, Jianbin Li, Chao‐Jun Li

и другие.

Chemical Science, Год журнала: 2022, Номер 13(19), С. 5465 - 5504

Опубликована: Янв. 1, 2022

C(sp 3 ) radicals (R˙) are of broad research interest and synthetic utility.

Язык: Английский

Процитировано

75
Radical 1,2-Nitrogen Migration Cascades of β-Bromo α-Amino Acid Esters to Access β-Amino Acid Motifs Enabled by Cooperative Ni/Diboron Catalysis DOI

Yu Hong,

Zi-Cheng Liao,

Jiajie Chen

и другие.

ACS Catalysis, Год журнала: 2024, Номер 14(8), С. 5491 - 5502

Опубликована: Март 28, 2024

Amino acid esters serve as crucial intermediates in protein synthesis and common structural elements biologically active natural compounds. Herein, we present an efficient radical cascade reaction involving 1,2-nitrogen migration C(sp2)–H intramolecular cyclization, enabling access to a diverse array of β-amino motifs. Upon cooperative Ni/diboron catalysis, π-system-independent 1,2-N-shift β-bromo α-amino is achieved, which allows the formation two new bonds, including C(sp3)–C(sp2) bond C(sp3)–N bond. The exhibits extensive substrate compatibility high diastereoselectivity proceeds without need for oxidants, toxic initiators, and/or elevated temperatures. It has been observed that diboron compounds both activating reagent inert C–N cleavage/migration reductant Ni catalytic cycle. This sheds light on remote N-functionalities π-systems. cascades followed by intermolecular halogenation or selenation are also demonstrated.

Язык: Английский

Процитировано

21
Advances in transition metal-free deborylative transformations of gem-diborylalkanes DOI Open Access
Woohyun Jo, Jun Hee Lee, Seung Hwan Cho

и другие.

Chemical Communications, Год журнала: 2021, Номер 57(36), С. 4346 - 4353

Опубликована: Янв. 1, 2021

This article highlights recent advances on the base-promoted deborylative carbon–carbon and carbon–boron bond-forming reactions using gem-diborylalkanes as sources of α-borylcabanions.

Язык: Английский

Процитировано

69
The Impact of Boron Hybridisation on Photocatalytic Processes DOI Creative Commons

Alessandro Marotta,

Callum E. Adams,

John J. Molloy

и другие.

Angewandte Chemie International Edition, Год журнала: 2022, Номер 61(38)

Опубликована: Июнь 24, 2022

Recently the fruitful merger of organoboron chemistry and photocatalysis has come to forefront organic synthesis, resulting in development new technologies access complex (non)borylated frameworks. Central success this combination is control boron hybridisation. Contingent on photoactivation mode, as its neutral planar form or tetrahedral boronate can be used regulate reactivity. This Minireview highlights current state art photocatalytic processes utilising compounds, paying particular attention role hybridisation for target transformation.

Язык: Английский

Процитировано

55
Pd/IPrBIDEA-Catalyzed Hydrodefluorination of gem-Difluorocyclopropanes: Regioselective Synthesis of Terminal Fluoroalkenes DOI
Huijun Qian,

Zachary P. Cheng,

Yani Luo

и другие.

Journal of the American Chemical Society, Год журнала: 2023, Номер 146(1), С. 24 - 32

Опубликована: Окт. 13, 2023

Developing new strategies to enable chemo- and regioselective reductions is an important topic in chemical research. Herein, efficient Pd/IPr

Язык: Английский

Процитировано

33
Ir‐Catalyzed Enantioselective Synthesis of gem‐Diborylalkenes Enabled by 1,2‐Boron Shift DOI

Jianfei Ge,

Xi‐Zhang Zou,

Xinru Liu

и другие.

Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(32)

Опубликована: Июнь 15, 2023

Abstract Asymmetric cross‐couplings based on 1,2‐carbon migration from B‐ate complexes have been developed efficiently to access valuable organoboronates. However, enantioselective reactions triggered by 1,2‐boron shift remained be unaddressed synthetic challenge. Here, Ir‐catalyzed asymmetric allylic alkylation enabled was developed. In this reaction, we disclosed that excellent enantioselectivities were achieved through an interesting dynamic kinetic resolution (DKR) process of carbonates at the elevated temperature. Notably, highly (bis‐boryl)alkenes array diversifications versatile molecules. Extensive experimental and computational studies conducted elucidate reaction mechanism DKR clarify origin enantioselectivities.

Язык: Английский

Процитировано

27
Diborodichloromethane as Versatile Reagent for Chemodivergent Synthesis of gem‐Diborylalkanes DOI

Tongchang Fang,

Liwei Wang, Miaomiao Wu

и другие.

Angewandte Chemie International Edition, Год журнала: 2023, Номер 63(3)

Опубликована: Дек. 8, 2023

Abstract The development of boron reagents is crucial for synthetic chemistry. Herein, we present a scalable and practical synthesis diborodichloromethane (DBDCM) through the reaction trichloromethyllithium with bis(pinacolato)diboron (B 2 pin ). resulting DBDCM reagent serves as basic unit construction various structurally diverse gem ‐diborylalkanes controllable C−Cl functionalizations. Moreover, have developed consecutive tetra‐functionalizations tertiary quaternary carbon containing molecules. use isotopically enriched 13 C‐chloroform 10 B enables C‐DBDCM B‐DBDCM reagents, which are beneficial convenient carbon‐13 boron‐10

Язык: Английский

Процитировано

25
Alkyl Radical Generation from Alkylboronic Pinacol Esters through Substitution with Aminyl Radicals DOI
Zhe Wang,

Nick Wierich,

Jingjing Zhang

и другие.

Journal of the American Chemical Society, Год журнала: 2023, Номер 145(16), С. 8770 - 8775

Опубликована: Апрель 14, 2023

Alkylboronic pinacol esters (APEs) are highly versatile reagents in organic synthesis. However, the direct generation of alkyl radicals from commonly used, bench-stable APEs has not been well explored. In this communication, radical through reaction with aminyl is reported. The readily generated by visible-light-induced homolytic cleavage N-N bond N-nitrosamines, and C occurs nucleohomolytic substitution at boron. As an application, efficient photochemical alkyloximation alkenes N-nitrosamines under mild conditions presented. A wide range primary, secondary, tertiary engage transformation that easily scaled up.

Язык: Английский

Процитировано

23