Examining the Scope of Deriving β-Aryl Enones from Enol Silanes as Ketone Equivalents via Pd(II)-Mediated Sequential Dehydrosilylation and Arylation DOI

Subba Rao Polimera,

Andivelu Ilangovan, Murugaiah A. M. Subbaiah

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(11), P. 7256 - 7271

Published: May 16, 2023

Silyl enol ethers were examined as a masked source of saturated ketones to derive β-aryl enones and their derivatives by dehydrosilylation generate in situ subsequent oxidative arylation with arylboronic acids transmetallation coupling partners using relayed Pd(II) catalysis one pot under base-free conditions. Oxygen was found be an efficient green oxidant enable both silanes arylation. Additionally, conditions can custom-designed take advantage aryl halides alternative arylating agents. The preparative scope investigated 35 examples (up 95% yield), mechanistic studies implied cationic Pd(II)-based catalytic system.

Language: Английский

Synthesis, reactions and application of chalcones: a systematic review DOI
Mona A. Shalaby, Sameh A. Rizk, Asmaa M. Fahim

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(26), P. 5317 - 5346

Published: Jan. 1, 2023

Chalcones, Reactions, Synthesis, Biological activity, Industrial application.

Language: Английский

Citations

49
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
Palladium Catalysis Enabled Sequential C(sp3)–H/C–C Activation: Access to Vinyl γ-Lactams DOI

Madhab Barman,

Manmath Mishra,

Santu Mandal

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(18), P. 3722 - 3726

Published: April 28, 2024

A Pd(II)-catalyzed tandem reaction of aliphatic amides with vinylcyclopropanes (VCPs) was accomplished by merging C(sp3)–H and C–C activation. The VCP revealed alkenylation/cyclization, followed ring opening via cleavage, delivering vinyl γ-lactams (E)-selectivity. role ligands, site-selectivity, functional group diversity, mechanistic insight, synthetic utilities are important practical features.

Language: Английский

Citations

5
Visible-light or sunlight photoredox-catalyzed β-selective acylation of alkenes to access α, β-unsaturated ketones DOI

Xun Yang,

Yuxuan Xiao, Ying Yin

et al.

Organic Chemistry Frontiers, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A general method for accessing α,β-unsaturated ketones through visible-light or sunlight photoredox-catalyzed β-selective acylation of alkenes has been developed.

Language: Английский

Citations

0
Promoting Catalytic C-Selective Sulfonylation of Cyclopropanols against Conventional O-Sulfonylation Using Readily Available Sulfonyl Chlorides DOI

Thangeswaran Ramar,

Andivelu Ilangovan, Murugaiah A. M. Subbaiah

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(19), P. 13553 - 13567

Published: Sept. 14, 2023

Against the backdrop of well-known O-sulfonylation cyclopropyl alcohols with sulfonyl chlorides, we examined feasibility conducting regioselective C-sulfonylation. By emulating an umpolung strategy-guided design, report for first time Cu(II)-catalyzed β-sulfonylation cyclopropanols by a mechanism that potentially involves oxidative addition radical to metal homoenolate. Unlike reported methods, this protocol allows practical synthetic route γ-keto sulfone building blocks from leveraging commercially available aryl- and alkyl-sulfonyl common reagents in organic chemistry laboratories. Using operationally simple open-flask conditions, preparative scope starting materials was demonstrated using array alkyl-substituted chlorides (43 examples, up 96% yield).

Language: Английский

Citations

8
Electrophilic Hydrazination of Cyclopropanols Using Azodicarboxylates via Copper(II) Catalysis: An Umpolung Strategy to Access β-Hydrazino Ketone Motifs DOI

Thangeswaran Ramar,

Andivelu Ilangovan, Nicholas A. Meanwell

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(21), P. 14596 - 14608

Published: Oct. 3, 2022

The scope of an umpolung approach to expand synthetic access bifunctional γ-keto hydrazine intermediates via electrophilic amination β-homoenolates derived from cyclopropanol precursors that took advantage azodicarboxylates or azodicarboxamides as electron-deficient nitrogen sources was examined. This new procedure avails commercially available readily accessible starting materials along with a ligand-free Cu(II) salt inexpensive catalyst. Using this operationally simple reaction, which proceeds under mild conditions (open-flask and ambient temperature) is suitable for multigram scale, preparative applications were established range aryl- alkyl-substituted cyclopropanols azodicarboxylate/azodicarboxamide substrates (26 examples, 74-95% yields). Further, the obtained products have been shown provide convenient γ-hydroxy hydrazide, γ-amino heterocyclic derivatives.

Language: Английский

Citations

9
Synthesis of Vicinal anti-Amino Alcohols from N-tert-Butanesulfinyl Aldimines and Cyclopropanols DOI Creative Commons
Sandra Hernández-Ibáñez,

Juan F. Ortuño,

Ana Sirvent

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(9), P. 6193 - 6204

Published: April 13, 2024

The stereoselective synthesis of vicinal amino alcohols derivatives from 1-substituted cyclopropanols and chiral

Language: Английский

Citations

1
Synthetic Access to α-Oxoketene Aminals by the Nucleophilic Addition of Enol Silane-Derived Palladium(II) Enolates to Carbodiimides DOI

Subba Rao Polimera,

Andivelu Ilangovan, Nicholas A. Meanwell

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(21), P. 14778 - 14792

Published: Oct. 26, 2022

Synthetically important α-oxoketene aminal intermediates can now be accessed from readily available and inexpensive carbodiimides as starting materials via the nucleophilic addition of palladium enolates derived enol silane precursors. This operationally simple method features mild reaction conditions, including open air atmosphere, ligand-free metal catalysis, broad substrate scope, multi-gram scalability. Select synthetic applications that take advantage enamine character aminals involve C-nucleophilic additions to electrophilic systems, an α,β-unsaturated ester, azo dicarboxylate, aralkyl halide, aldehyde, are demonstrated.

Language: Английский

Citations

3
Examining the Scope of Deriving β-Aryl Enones from Enol Silanes as Ketone Equivalents via Pd(II)-Mediated Sequential Dehydrosilylation and Arylation DOI

Subba Rao Polimera,

Andivelu Ilangovan, Murugaiah A. M. Subbaiah

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(11), P. 7256 - 7271

Published: May 16, 2023

Silyl enol ethers were examined as a masked source of saturated ketones to derive β-aryl enones and their derivatives by dehydrosilylation generate in situ subsequent oxidative arylation with arylboronic acids transmetallation coupling partners using relayed Pd(II) catalysis one pot under base-free conditions. Oxygen was found be an efficient green oxidant enable both silanes arylation. Additionally, conditions can custom-designed take advantage aryl halides alternative arylating agents. The preparative scope investigated 35 examples (up 95% yield), mechanistic studies implied cationic Pd(II)-based catalytic system.

Language: Английский

Citations

1