Stereochemical modulation of ketyl radical cyclization enabled by pyridine-boryl radicals: catalytic diastereoselective synthesis of trans-2-alkyl-1-indanols DOI

Somi Kim,

Junhyuk Jo,

Sunggi Lee

и другие.

Chemical Communications, Год журнала: 2023, Номер 59(80), С. 11983 - 11986

Опубликована: Янв. 1, 2023

Previously available ketyl radical cyclization conditions suffer from low and uncontrollable diastereoselectivity because of the absence reagent-substrate interactions. In this report, stereochemical modulation was accomplished by taking advantage pyridine-boryl radical, which leaves synthetically modifiable boronate moiety on carbonyl oxygen near reacting center during stereo-determining step. consequence, a catalytic diastereoselective synthesis trans-2-substituted-1-indanols achieved in presence sterically congested six-membered diboronic ester an efficient hydrogen atom donor.

Язык: Английский

Diboron(4)‐Catalyzed Remote [3+2] Cycloaddition of Cyclopropanes via Dearomative/Rearomative Radical Transmission through Pyridine DOI

Ming Xu,

Zhijun Wang, Zhaohui Sun

и другие.

Angewandte Chemie International Edition, Год журнала: 2022, Номер 61(52)

Опубликована: Ноя. 8, 2022

Abstract Ring structures such as pyridine, cyclopentane or their combinations are important motifs in bioactive molecules. In contrast to previous cycloaddition reactions that necessitated a directly bonded initiating functional group, this work demonstrated novel through‐(hetero)arene radical transmission concept for selective activation of remote bond. An efficient, metal‐free and atom‐economical [3+2] between 4‐pyridinyl cyclopropanes alkenes alkynes has been developed modular synthesis pyridine‐substituted cyclopentanes, cyclopentenes bicyclo[2.1.1]hexanes difficult access using known methods. This complexity‐building reaction was catalyzed by very simple inexpensive diboron(4) compound took place via dearomative/rearomative processes. The substrate scope broad more than 100 new compounds were prepared generally high yields. Mechanistic experiments density function theory (DFT) investigation supported relay catalytic cycle involving alkylidene dihydropyridine intermediates boronyl transfer.

Язык: Английский

Процитировано

107

Synthesis of Tetrahydro-indolones through Rh(III)-Catalyzed [3 + 2] Annulation of Enaminones with Iodonium Ylides DOI

Mingshuai Zhang,

Longkun Chen,

Haifeng Sun

и другие.

Organic Letters, Год журнала: 2023, Номер 25(40), С. 7298 - 7303

Опубликована: Окт. 3, 2023

An unprecedented protocol for a Rh(III)-catalyzed [3 + 2] annulation from simple and readily available enaminones iodonium ylides has been developed. The novel strategy allows access to new class of structurally diverse tetrahydro-indolones with high efficiency broad substrate scope. In addition, this transformation represents the first example selective alkenyl C–H bond functionalization enaminones. Finally, potential applications are demonstrated through gram-scale reaction late-stage modification.

Язык: Английский

Процитировано

38

Rh(III)-Catalyzed [3 + 2] Annulation/Pinacol Rearrangement Reaction of Enaminones with Iodonium Ylides: Direct Synthesis of 2-Spirocyclo-pyrrol-3-ones DOI

Mingshuai Zhang,

Longkun Chen,

Haifeng Sun

и другие.

Organic Letters, Год журнала: 2023, Номер 25(39), С. 7214 - 7219

Опубликована: Сен. 26, 2023

A novel Rh(III)-catalyzed cascade alkenyl C-H activation/[3 + 2] annulation/pinacol rearrangement reaction of enaminones with iodonium ylides has been developed. This methodology provides a new and straightforward synthetic strategy to afford highly functionalized 2-spirocyclo-pyrrol-3-ones in satisfactory yield from readily available starting materials under mild conditions. Moreover, gram-scale reactions further derivatization experiments are implemented demonstrate the potential utility this developed approach.

Язык: Английский

Процитировано

33

Selective synthesis of pyridazin-fused chromones and 3-pyridazinyl chromones through intermolecular chromone annulation of o-hydroxyphenylenaminones with aryldiazonium salts DOI
Siyu Song,

Zhilai Zhang,

Menglin Peng

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(14), С. 3906 - 3912

Опубликована: Янв. 1, 2024

A chemodivergent and skeleton-controllable annulation reactions of readily available o -HPEs aryldiazonium salts was described for the synthesis highly functionalized pyridazine-fused chromones with high antiviral activity higher safety.

Язык: Английский

Процитировано

11

I2-DMSO mediated tetra-functionalization of enaminones for the construction of novel furo[2′,3′:4,5]pyrimido[1,2-b]indazole skeletons via in situ capture of ketenimine cations DOI
You Zhou, Li‐Sheng Wang,

Shuang‐Gui Lei

и другие.

Chinese Chemical Letters, Год журнала: 2024, Номер 36(1), С. 109799 - 109799

Опубликована: Март 20, 2024

Язык: Английский

Процитировано

10

Copper‐Catalyzed Oxidative [1+2+1+2] Cascade Cyclization of N,N‐Dimethyl Enaminones with Benzylamines: A Facile Access to Functionalized 1,4‐Dihydropyridines DOI

Yulin Sun,

Zhangmengjie Chai,

Donghan Liu

и другие.

Chemistry - A European Journal, Год журнала: 2023, Номер 29(28)

Опубликована: Фев. 24, 2023

Using benzylamines as the C4 source of 1,4-dihydropyridines (1,4-DHPs), a Cu-catalyzed oxidative [1+2+1+2] cascade cyclization for synthesis 1,4-DHPs was firstly developed. A broad range easily available N,N-dimethyl enaminones and are employed smoothly to provide diverse with high efficiency. This method is performed by one-pot C(sp3 )-H bond functionalization/C(sp3 )-N cleavage/cyclization strategy form simultaneously two )-C(sp2 ) bonds, C(sp2 1,4-DHP ring.

Язык: Английский

Процитировано

20

Synthesis of Indolizines via Tf2O-Mediated Cascade Reaction of Pyridyl-enaminones with Thiophenols/Thioalcohols DOI
Changyuan Zhang, Wei Wang,

Xuncheng Zhu

и другие.

Organic Letters, Год журнала: 2023, Номер 25(7), С. 1192 - 1197

Опубликована: Фев. 13, 2023

A cost-effective, highly regioselective and metal-free version for the synthesis of indolizine derivatives by means Tf2O-mediated cascade reaction pyridyl-enaminones thiophenols/thioalcohols under mild conditions has been reported. Diverse electron-rich could be obtained in up to 94% yield via selective 1,4-addition vinyl iminium triflate tandem cyclization/aromatization, which allowed simultaneous construction C–N C–S/and one example C–Se bonds.

Язык: Английский

Процитировано

15

Rh(iii)-catalyzed cascade annulation reaction of N,N-dimethyl enaminones with iodonium ylides to give substituted isocoumarins DOI

Mingshuai Zhang,

Longkun Chen,

Donghan Liu

и другие.

New Journal of Chemistry, Год журнала: 2023, Номер 47(26), С. 12274 - 12278

Опубликована: Янв. 1, 2023

A wide variety of isocoumarin derivatives are easily constructed via a Rh( iii )-catalyzed C–H bond activation/annulation cascade reaction.

Язык: Английский

Процитировано

15

Rh(iii)-catalyzed selective mono- and dual-functionalization/cyclization of 1-aryl-5-aminopyrazoles with iodonium ylides DOI

Longkun Chen,

Mingshuai Zhang,

Meichen Liu

и другие.

Chemical Communications, Год журнала: 2023, Номер 60(4), С. 432 - 435

Опубликована: Дек. 5, 2023

Highly functionalized benzodiazepine skeletons were efficiently synthesized via a Rh( iii )-catalyzed selective mono- and dual-C–H bond functionalization/cyclization reaction between readily available 1-aryl-5-aminopyrazoles iodonium ylides under.

Язык: Английский

Процитировано

14

Synthesis of Functionalized 3‐(1H‐Isochromen)‐chromones via Ag2O‐Catalyzed Cascade Cyclization Reaction of o‐Hydroxyarylenaminones with o‐Alkynylbenzaldehydes DOI

Mingshuai Zhang,

Zhuoyuan Liu,

Longkun Chen

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2022, Номер 364(24), С. 4440 - 4446

Опубликована: Дек. 2, 2022

Abstract A silver‐catalyzed protocol for the synthesis of 3‐(1 H ‐isochromen)‐chromones is described. The method involves an initial 6‐endo‐dig cyclization o ‐alkynylbenzaldehydes and domino C−H alkylation chromone annulation ‐hydroxyarylenaminones, which enables installation 1 ‐isochromen in a single structure. This synthetic strategy advantageous excellent regioselectivity, step economy, concise one‐pot methodology, gram‐scale synthesis, as well high bond‐forming efficiency. magnified image

Язык: Английский

Процитировано

22