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

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(7), P. 4508 - 4523

Published: March 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.

Language: Английский

Photoredox-Catalyzed 1,4-Peroxidation–Sulfonylation of Enynones: A Three-Component Radical Coupling Approach for the Synthesis of Highly Functionalized Allenes DOI

Divya Bhatt,

Kosei Miyake,

Shuichi Nakamura

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(15), P. 2955 - 2959

Published: April 3, 2024

An Eosin Y-catalyzed visible light-promoted 1,4-peroxidation–sulfonylation of enynones was achieved to give tetrasubstituted allenes. The photoredox catalysis Y allowed the concomitant formation peroxy and sulfonyl radicals, where preferential radical addition alkene moiety resulted in subsequent α-keto radical–sulfonyl cross couplings. developed demonstrates a regioselective 1,4-diradical strategy, opening up new possibility diradical functionalization conjugate systems.

Language: Английский

Citations

9

Strained cycloalkanols in C–C bond formation reactions: a boon in disguise! DOI
Neha Jha, P. Mishra, Manmohan Kapur

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(19), P. 4941 - 4971

Published: Jan. 1, 2023

A summary of the various ring opening reactions strained and unstrained cycloalkanols is elaborated in present review. Key emphasis on reactivities pertaining to cyclopropanols, cyclobutanols higher analogues provided.

Language: Английский

Citations

14

Stereoselective Iron-Catalyzed Alkylation of Enamides with Cyclopropanols via Oxidative C(sp2)–H Functionalization DOI

Xing Zhang,

Tianming Yang,

Lu-Min Hu

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(47), P. 8677 - 8682

Published: Nov. 17, 2022

Established herein is a radical-mediated C–H alkylation of enamides with cyclopropanols. An environmentally benign catalytic system iron salt and air used to permit the oxidative coupling process. The protocol demonstrates broad substrate scope, allowing stereoselective synthesis alkylated enamides. value this strategy further reflected by late-stage diversification complex cyclopropanol-containing molecules downstream transformations. Mechanistic studies reveal dual role in reaction.

Language: Английский

Citations

22

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

Seyedeh Pegah Aledavoud,

Azadeh Fakhrioliaei

et al.

ChemistrySelect, Journal Year: 2023, Volume and Issue: 8(32)

Published: Aug. 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.

Language: Английский

Citations

12

Recent Advances in Non-Precious Metal Catalysis DOI
Hao Wu, Bo Qu, Thach T. Nguyen

et al.

Organic Process Research & Development, Journal Year: 2022, Volume and Issue: 26(8), P. 2281 - 2310

Published: Aug. 2, 2022

This review provides a summary of recently published developments in the field nonprecious metal catalysis (NPMC) and highlights range synthetic applications captured research between July October 2021. is an installment series on this area briefing Ni, Cu, Fe, Co catalysis. There has been evident increase publications NPMC, which indicates widespread interest among laboratories academia industry development utilization catalytic these metals.

Language: Английский

Citations

18

Arylation of Cyclopropanol with Pyrrole: Asymmetric Synthesis of Indolizidine 167B, Indolizidine 209D, and Monomorine I DOI

Shuangwei Liu,

Xiaojiao Su,

Dan Jiang

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(12), P. 2058 - 2062

Published: March 17, 2023

A Fe(NO3)3-mediated ring-opening arylation of cyclopropanol with the electron-rich pyrrole has been developed, which might proceed through oxidative radical ring opening followed by cyclization to motif and then aromatization. This method enables direct without prefunctionalization thus allows rapid access a diverse array chiral 5,6,7,8-tetrahydroindolizines from easily available amino acid esters. The synthetic utility demonstrated asymmetric synthesis alklaoids (-)-indolizidine 167B, (+)-indolizidine 209D, (+)-monomorine I, natural product analogue.

Language: Английский

Citations

11

TEMPO Mediated Cyclopropanols Ring Opening C−N Cross‐Coupling with Nitrogen Nucleophiles DOI
Jun‐Long Zhan, Lin Zhu, Wei Ren

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(10), P. 1678 - 1684

Published: April 28, 2023

Abstract A feasible and umpolung strategy for the synthesis of structurally diverse β ‐amino ketones has been achieved through TEMPO mediated C−N coupling cyclopropanols with nitrogen nucleophiles. Mechanism studies indicated that in situ generated enones derived from are key intermediates play multiple roles, including radical initiator, trapping reagent, a porter ‐hydrogen an base. This protocol features broad substrate scope, good scalability to excellent yields provides alternative complementary approach important ketone scaffolds under metal additive‐free conditions. magnified image

Language: Английский

Citations

11

Iron-Catalyzed Oxidative Rearrangement of Cyclopropanone Hemiaminals: General Access to Pyrroloindolones from Indoles DOI
Roger Machín Rivera,

Zack R. Ferrin,

Vincent N. G. Lindsay

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(22), P. 4738 - 4743

Published: May 29, 2024

A concise synthetic approach to medicinally relevant pyrroloindolones and related fused heterocycles is reported via the diastereoselective

Language: Английский

Citations

4

Three-Component Reaction of Cyclopropanols, DABSO, and N-(Sulfonyl)acrylamides: Preparation of Sulfone-Bridged 1,7-Dicarbonyl Compounds DOI
Fei Chen, Li Xiao,

Ke-Ying Liu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(34), P. 7170 - 7175

Published: Aug. 19, 2024

A cascade reaction of cyclopropyl alcohols, DABSO (1,4-diazoniabicyclo[2.2.2]octane-1,4-disulfinate), and N-(sulfonyl)acrylamides has been developed. This tandem process went through a cyclopropanol ring opening Michael addition sequence. The γ-keto sulfinate generated from the between serves as nucleophilic reagent, N-(sulfonyl)acrylamide is used acceptor. By utilizing this strategy, multitudinous sulfone-bridged 1,7-dicarbonyl compounds that contain both β-sulfonyl amide unit sulfone skeleton were conveniently synthesized.

Language: Английский

Citations

4

Deconstructive Cyanomethylation Enabled by Radical Cross‐Coupling through Multiple C−C Bond and C−H Bond Cleavage DOI

Changzhen Yin,

Wei Liu, Qiang Wu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(7), P. 1072 - 1081

Published: March 17, 2023

Abstract Being in its infancy, radical cross‐coupling is highly efficient for C−C bond construction, though suffers from selectivity problems and limited reaction types. New methodologies to realize selectively are desired. Herein, an iron catalyzed deconstructive cyanomethylation of unstrained cyclic linear alcohols with acetonitrile has been developed through cross‐coupling. The unprecedented method enables a ring‐opening functionalization cyclohexanols produce α‐cyanomethyl ketones. Notably, the challenging involves twice single cleavage β‐scission alkoxyl intermediates, C( sp 3 )−H transformation via hydrogen atom transfer (HAT) procedures, resulting two carbon species that process form new )−C( ) selectively. α‐arylketo α‐aryl substituted tertiary can also be applied as substrates, leading terminal cyano‐functionalized products, ketone leaving fragment. Mechanistically, procedure generate chlorine in‐situ formed intermediate cycloalkyl hypochlorite was suggested. magnified image

Language: Английский

Citations

9