Synthesis and Applications of π-Conjugation-Extended Vinyl Sulfoxonium Ylides

S Kumar, DS Davas, K Bar, DK Gopalakrishnan… - Organic …, 2023 - ACS Publications
Herein, we report the synthesis of π-conjugation-extended vinyl sulfoxonium ylides from
vinyl sulfoxonium ylide and electron-deficient alkynes. The new dienoate ylides are used in …

Site Reversal in Nucleophilic Addition to 1, 2, 3-Triazine 1-Oxides

L De Angelis, GC Haug, G Rivera… - Journal of the …, 2023 - ACS Publications
One of the most important reactions of 1, 2, 3-triazines with a dienophile is inverse electron
demand Diels–Alder (IEDDA) cycloaddition, which occurs through nucleophilic addition to …

Chiral Magnesium Complex-Catalyzed Asymmetric Cyclization of Vinyl Diazo Compounds with Phenol Derivatives via Noncarbene Pathways

Q Jiang, YQ Deng, XL Luo, ZH Dong, Y Zhou… - ACS …, 2024 - ACS Publications
Vinyl diazo compounds are of great interest since they can both serve as carbene
precursors to react with nucleophiles and act as nucleophiles to react with electrophiles via …

[HTML][HTML] Expanded access to vinyldiazo compounds and their catalytic enantioselective applications

M Bao, L De Angelis, MS Rada, M Baird, H Arman… - Chem Catalysis, 2023 - cell.com
The catalytic uses of metal carbenes for addition, insertion, and cycloaddition reactions are
dependent on their carbene precursor. The limited methods available for the preparation of …

Construction of Diazo Compounds via Catalytic [3+ 2] Annulation of Vinyldiazoacetates and Their Synthetic Applications

M Bao, DV Navarrete Carriola, D Wherritt… - ACS Catalysis, 2024 - ACS Publications
Highly selective formal [3+ 2]-cycloaddition of vinyldiazoacetates with quinone ketals and
quinoneimine ketals has been accomplished at room temperature with catalytic amounts of …

Synthesis of Cyclopenta[b]indoles via Sc(III)-Catalyzed Annulation of Vinyl Diazoacetates with Indole-Derived Unsaturated Imines

Q Jiang, T Yang, Q Li, GM Liang, Y Liu, CY He… - Organic …, 2023 - ACS Publications
A Lewis acid Sc (OTf) 3-catalyzed annulation reaction of vinyl diazoacetates with in situ
formed α, β-unsaturated imines for the preparation of indole-fused tricyclic rings has been …

Inverse Electron Demand Diels–Alder-Type Heterocycle Syntheses with 1, 2, 3-Triazine 1-Oxides: Expanded Versatility

S Biswas, L De Angelis, G Rivera, H Arman… - Organic …, 2023 - ACS Publications
1, 2, 3-Triazine 1-oxides are remarkably effective substrates for inverse electron demand
Diels–Alder reactions. Formed from vinyldiazoacetates via reaction with tert-butyl nitrite …

DBU-Promoted tandem cyclization of ynones and diazo compounds: direct synthesis of eight-membered cyclic ethers

XC Xu, Y Gong, J Wang, YR Yuan, YL Zhao - Organic Letters, 2023 - ACS Publications
A novel DBU-promoted tandem cyclization reaction of ynones with diazo compounds as the
N-terminal electrophiles has been developed. The reaction provides a simple and efficient …

Cyclization of Vinyl Diazo Compounds with Benzofuran-Derived Azadienes Enabled by NaBArF4

T Yang, Q Jiang, CM Wang, SL Li, CY He… - Organic …, 2023 - ACS Publications
An unprecedented cycloaddition of vinyl diazo compounds with benzofuran-derived
azadienes catalyzed by rarely independently used NaBArF4 has been established …

Metal Carbene-Directed Intramolecular Vinylogous Reactions of Vinyldiazoacetates

MS Rada, DM Bystrov, DN Carriola, D Wherritt… - ACS …, 2024 - ACS Publications
Intramolecular addition reactions of electrophilic metallovinylcarbenes with nucleophiles that
do not have access to the carbene center undergo addition to the vinylogous position …