β‐Diazocarbonyl Compounds: Synthesis and their Rh(II)‐Catalyzed 1,3 C−H Insertions DOI
Liyin Jiang, Zhaofeng Wang,

Melanie Armstrong

et al.

Angewandte Chemie International Edition, Journal Year: 2020, Volume and Issue: 60(11), P. 6177 - 6184

Published: Dec. 4, 2020

Abstract Herein, we describe the first electrophilic diazomethylation of ketone silyl enol ethers with diazomethyl‐substituted hypervalent iodine reagents that gives access to unusual β‐diazocarbonyl compounds. The potential this unexplored class diazo compounds for development new reactions was demonstrated by discovery a rare Rh‐catalyzed intramolecular 1,3 C−H carbene insertion led complex cyclopropanes excellent stereocontrol.

Language: Английский

Photoredox Catalysis Enables Decarboxylative Cyclization with Hypervalent Iodine(III) Reagents: Access to 2,5-Disubstituted 1,3,4-Oxadiazoles DOI
Jian Li,

Xue-Chen Lu,

Yue Xu

et al.

Organic Letters, Journal Year: 2020, Volume and Issue: 22(24), P. 9621 - 9626

Published: Dec. 1, 2020

A novel approach to 2,5-disubstituted 1,3,4-oxadiazoles derivatives via a decarboxylative cyclization reaction by photoredox catalysis between commercially available α-oxocarboxylic acids and hypervalent iodine(III) reagent is described. This powerful transformation involves the coupling two different kinds of radical species formation C–N C–O bonds.

Language: Английский

Citations

45
Visible Light‐Induced [3+2] Cyclization Reactions of Hydrazones with Hypervalent Iodine Diazo Reagents for the Synthesis of 1‐Amino‐1,2,3‐Triazoles DOI

Dong Jun-ying,

He Wang,

Shukuan Mao

et al.

Advanced Synthesis & Catalysis, Journal Year: 2021, Volume and Issue: 363(8), P. 2133 - 2139

Published: Feb. 19, 2021

Abstract In this study, visible‐light‐induced [3+2] cyclization reactions of hydrazones with hypervalent iodine diazo reagents as diazomethyl radical precursors are reported. Mild reaction conditions, a broad substrate scope, and excellent functional group compatibility were observed. Furthermore, the synthetic utility was demonstrated by gram‐scale synthesis elaboration to several value‐added products. This protocol broadens scope chemistry, is applicable late‐stage functionalization natural magnified image

Language: Английский

Citations

34
Catalytic alkene skeletal modification for the construction of fluorinated tertiary stereocenters DOI Creative Commons
Liyin Jiang, Pau Sarró, Wei Jie Teo

et al.

Chemical Science, Journal Year: 2022, Volume and Issue: 13(15), P. 4327 - 4333

Published: Jan. 1, 2022

We report a previously unknown disconnection approach to valuable fluorinated tertiary stereocenters based on the skeletal modification of 1,1-disubstituted alkenes by Rh-catalyzed carbyne transfer.

Language: Английский

Citations

25
α-Diazo-λ3-iodanes and α-diazo sulfonium salts: the umpolung of diazo compounds DOI Creative Commons

Sven Timmann,

Manuel Alcarazo

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(52), P. 8032 - 8042

Published: Jan. 1, 2023

This article reviews the strategies available to achieve umpolung of diazocompounds and synthetic applications such compounds.

Language: Английский

Citations

17
β‐Diazocarbonyl Compounds: Synthesis and their Rh(II)‐Catalyzed 1,3 C−H Insertions DOI
Liyin Jiang, Zhaofeng Wang,

Melanie Armstrong

et al.

Angewandte Chemie International Edition, Journal Year: 2020, Volume and Issue: 60(11), P. 6177 - 6184

Published: Dec. 4, 2020

Abstract Herein, we describe the first electrophilic diazomethylation of ketone silyl enol ethers with diazomethyl‐substituted hypervalent iodine reagents that gives access to unusual β‐diazocarbonyl compounds. The potential this unexplored class diazo compounds for development new reactions was demonstrated by discovery a rare Rh‐catalyzed intramolecular 1,3 C−H carbene insertion led complex cyclopropanes excellent stereocontrol.

Language: Английский

Citations

37