Orchestrating a β-Hydride Elimination Pathway in Palladium(II)-Catalyzed Arylation/Alkenylation of Cyclopropanols Using Organoboron Reagents DOI

Thangeswaran Ramar,

Murugaiah A. M. Subbaiah, Andivelu Ilangovan

и другие.

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(7), С. 4508 - 4523

Опубликована: Март 15, 2022

The scope of chemoselective β-hydride elimination in the context arylation/alkenylation homoenolates from cyclopropanol precursors using organoboronic reagents as transmetalation coupling partners was examined. reaction optimization paradigm revealed a simple ligand-free Pd(II) catalytic system to be most efficient under open air conditions. preparative scope, which investigated with 48 examples, supported applicability this wide range substrates tolerating variety functional groups while delivering β-substituted enone and dienone derivatives 62-95% yields.

Язык: Английский

Metal-Catalyzed Transformations of Cyclopropanols via Homoenolates DOI Open Access
Yoshiya Sekiguchi, Naohiko Yoshikai

Bulletin of the Chemical Society of Japan, Год журнала: 2020, Номер 94(1), С. 265 - 280

Опубликована: Сен. 28, 2020

Abstract Metal homoenolates represent uniquely useful organometallic intermediates in synthetic chemistry, allowing umpolung synthesis of β-functionalized carbonyl compounds. While siloxycyclopropanes had been established as reliable precursors to homoenolates, often stoichiometric, for diverse carbon–carbon bond forming reactions, unprotected cyclopropanols have emerged alternative and attractive catalytically generated, carbon–heteroatom bond-forming reactions. This review article provides an overview the development such homoenolate transformations, classified with respect metals involved cyclopropane ring opening.

Язык: Английский

Процитировано

56

Iron-Catalyzed Ring-Opening Reactions of Cyclopropanols with Alkenes and TBHP: Synthesis of 5-Oxo Peroxides DOI

Chenhao Lou,

Xin Wang, Leiyang Lv

и другие.

Organic Letters, Год журнала: 2021, Номер 23(19), С. 7608 - 7612

Опубликована: Сен. 16, 2021

The ring opening of cyclopropanols is rarely used in multicomponent reactions. Herein we report the three-component reaction with alkenes and tert-butyl hydroperoxide (TBHP) catalyzed by an iron catalyst. This protocol enables incorporation both β-carbonyl fragment a peroxy unit across C═C double bond regioselectively, thus allowing efficient, facile access to 5-oxo peroxides. Modification biologically active molecules various downstream derivatizations peroxides are also demonstrated.

Язык: Английский

Процитировано

37

Palladium-catalyzed selective C–C bond cleavage and stereoselective alkenylation between cyclopropanol and 1,3-diyne: one-step synthesis of diverse conjugated enynes DOI Creative Commons
Bedadyuti Vedvyas Pati, Asit Ghosh, Komal Yadav

и другие.

Chemical Science, Год журнала: 2022, Номер 13(9), С. 2692 - 2700

Опубликована: Янв. 1, 2022

Palladium-catalyzed tandem activation and functionalization of readily accessible cyclopropanols have been demonstrated to access valuable conjugated enynes from 1,3-diynes with high stereo-selectivity.

Язык: Английский

Процитировано

28

Rh-Catalyzed cascade C–H activation/C–C cleavage/cyclization of carboxylic acids with cyclopropanols DOI
Siqi Wang,

Erfei Miao,

Hao Wang

и другие.

Chemical Communications, Год журнала: 2021, Номер 57(48), С. 5929 - 5932

Опубликована: Янв. 1, 2021

Merging both C–H and C–C activation in a tandem process is highly appealing but marked challenge.

Язык: Английский

Процитировано

30

Looking deep into C–H functionalization: the synthesis and application of cyclopentadienyl and related metal catalysts DOI
Guilherme A. M. Jardim, Renato L. Carvalho, Mateus P. Nunes

и другие.

Chemical Communications, Год журнала: 2022, Номер 58(19), С. 3101 - 3121

Опубликована: Янв. 1, 2022

This feature review is focused on recent key applications of commonly used transition-metal Cp-type catalysts for C–H bond functionalizations.

Язык: Английский

Процитировано

23

Phosphine-Catalyzed Stereoselective Ring-Opening Addition of Cyclopropenones with Nucleophiles DOI
Lulu Yang, Xin He, Jiao Jiao

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(13), С. 8722 - 8737

Опубликована: Июнь 14, 2023

A phosphine-catalyzed ring-opening addition reaction of cyclopropenones with a variety nucleophiles (NuH), including oxygen-, nitrogen-, sulfur-, and carbon-based ones, has been investigated, which produces potentially useful α,β-unsaturated carbonyl derivatives in high yields (up to 99%), regioselectivity, exclusive E-selectivity. The proceeds efficiency under very mild conditions using only 1 mol % PPh3 as the catalyst at room temperature. method is also amenable for synthesis deuterated alkenes when (NuD) are employed. mechanism investigated by experiments DFT calculations, suggests an α-ketenyl phosphorus ylide key intermediate catalytic cycle that captures stereoselective manner.

Язык: Английский

Процитировано

12

Ring‐Opening Cross‐Coupling/Cyclization Reaction of Cyclopropanols with Organic Compounds DOI
Fatemeh Doraghi,

Seyedeh Pegah Aledavoud,

Azadeh Fakhrioliaei

и другие.

ChemistrySelect, Год журнала: 2023, Номер 8(32)

Опубликована: Авг. 23, 2023

Abstract Cyclopropanols, due to their particular chemistry, can participate in various synthetic reactions with retention or cleavage of the strained three‐membered ring. Direct cross‐coupling ring‐opening reaction such molecules access organic compounds, as ketones has great importance medicinal chemistry and material sciences. Hence, coupling reaction/cyclization cyclopropanols for constructing new valuable presence a transition metal catalyst under metal‐free conditions is described this context. The features are discussed, mechanisms challenging highlighted.

Язык: Английский

Процитировано

12

Redox-Neutral Cobalt(III)-Catalyzed C–H Activation/Annulation of α,β-Unsaturated Oxime Ether with Alkyne: One-Step Access to Multisubstituted Pyridine DOI
Smruti Ranjan Mohanty, Bedadyuti Vedvyas Pati, Shyam Kumar Banjare

и другие.

The Journal of Organic Chemistry, Год журнала: 2020, Номер 86(1), С. 1074 - 1083

Опубликована: Дек. 22, 2020

A redox neutral Co(III)-catalyzed annulation of α,β-unsaturated oxime ether with alkyne has been reported. Multisubstituted pyridines were synthesized in good yields without the use any heavy metal oxidants. The developed methodology tolerates a variety functional groups. Notably, this transformation applied to late-stage modification bioactive molecule dehydropregnenolone.

Язык: Английский

Процитировано

28

Cobalt-catalyzed atom-economical, diastereo- and enantioselective coupling of aldimines and cyclopropanols DOI

Zhikun Liang,

Qinglei Chong,

Fanke Meng

и другие.

Science China Chemistry, Год журнала: 2021, Номер 64(10), С. 1750 - 1755

Опубликована: Авг. 30, 2021

Язык: Английский

Процитировано

25

Palladium-Catalyzed C–C Bond Activation of Cyclopropenone: Modular Access to Trisubstituted α,β-Unsaturated Esters and Amides DOI
Tanmayee Nanda, Pragati Biswal, Bedadyuti Vedvyas Pati

и другие.

The Journal of Organic Chemistry, Год журнала: 2021, Номер 86(3), С. 2682 - 2695

Опубликована: Янв. 11, 2021

Strain-driven palladium/N-heterocyclic carbene-catalyzed C–C bond activation of diphenylcyclopropenone (DPC) has been explored for one-step access to trisubstituted α,β-unsaturated esters and amides. The designed transformation works under mild conditions providing exclusively a single stereoisomer. Mechanistic studies support the oxidative addition cyclopropenone in-situ-generated Pd(0) intermediate. We have proved that vinylic hydrogen in product is coming from phenol/aniline through deuterium-labeling studies. Late-stage functionalization bioactive molecules such as procaine, estrone, hymecromone demonstrates robustness this protocol.

Язык: Английский

Процитировано

24