Metal‐Catalyzed Coupling of N‐Tosylhydrazones with Compounds Containing C‐H/Heteroatom‐H Bonds DOI

Akanksha Akanksha,

Ajaya Kumar Singh,

Anupama Asthana

et al.

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 16, 2024

Abstract The present review covers various advances in the field of metal‐catalyzed coupling N ‐tosylhydrazones with compounds containing C−H/heteroatom‐H bonds, including transition metal catalysts i. e., Pd, Rh, Cu, Ag, Ni and Co resulting alkylated, alkenylated, alkynylated, allenylated, annulated many other products. A carbene migratory insertion process play a key role carbon‐carbon single bond (C−C) double (C=C) formation undergoes variety cascade reactions to synthesize wide scope pharmaceutically medicinally valuable scaffoldings.

Language: Английский

Weak‐Chelation Assisted Regioselective Indole C(4)‐Alkynylation via Six‐Membered Cobaltacycle Intermediate DOI

Sofaya Joshi,

Riya Dutta, Shyam Kumar Banjare

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(6), P. 1341 - 1347

Published: Jan. 13, 2024

Abstract Herein a regioselective indole C4‐alkynylation has been uncovered utilizing an earth‐abundant cobalt(III)‐catalyst. For this process, (bromoethynyl)benzene was used as alkynylating agent. Also, after screening various amide‐protected chelating groups we found dimethyl‐amide is optimal for the in‐situ generation of cobaltacycle intermediate. The six‐membered intermediate detected through high‐resolution mass spectrometry HRMS, which key conversion. Further, mechanistic studies were performed such KIE experiments, and reactions with radical scavengers, based on results plausible mechanism proposed. Moreover, to show application methodology, product oxidized diketone, monoketone, alkene, alkane further derivatized tricycle derivative, core structure many natural products.

Language: Английский

Citations

5
Transient Directing Group-Assisted Palladium-Catalyzed C4-Alkynylation of Indoles DOI

Shuqi Guo,

Huanfeng Jiang,

Shaorong Yang

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 10, 2025

Pd-catalyzed C4-selective alkynylation of indoles was established by employing glycine as a transient directing group. This reaction exhibits high regioselectivity with the tolerance wide scope functional groups to afford diverse alkynylated in moderate good yields. Moreover, readily accessible scale-up synthesis and further decorations achieve multifunctionalized demonstrate synthetic potential this protocol.

Language: Английский

Citations

0
Transition-Metal-Catalyzed Directed C8–H Carbon–Carbon Bond Formation in Quinolines and 1,2,3,4-Tetrahydroquinolines DOI
Tharmalingam Punniyamurthy, Shubhajit Basak, Tripti Paul

et al.

Synthesis, Journal Year: 2023, Volume and Issue: 55(21), P. 3454 - 3469

Published: March 20, 2023

Abstract C8-Substituted quinoline (QN) and 1,2,3,4-tetrahydroquinoline (THQ) scaffolds are featured in numerous bioactive compounds natural products. Appreciable efforts have been made towards the development of elegant techniques to functionalize C8–H bond QNs THQs. The transition-metal-catalyzed chelation-assisted C–H activation strategy has emerged as an effective synthetic tool among existing methods. This review focuses on recent advances directed carbon–carbon forming reactions for functionalization THQs (till February 2023). discussion categorized based type reaction. 1 Introduction 2 Acylation 3 Alkylation 4 Alkenylation 5 Alkynylation 6 Allylation 7 Annulation 8 Arylation 9 Conclusion Outlook

Language: Английский

Citations

7
Transition‐Metal‐Catalyzed Directed C−H Functionalization in/on Water DOI Open Access
Tariq A. Shah, Tanumay Sarkar,

Subhradeep Kar

et al.

Chemistry - An Asian Journal, Journal Year: 2023, Volume and Issue: 19(1)

Published: Nov. 6, 2023

Abstract Directing group assisted C−H bond functionalization using transition‐metal‐catalysis has emerged as a reliable synthetic tool for the construction of regioselective carbon‐carbon/heteroatom bonds. Off late, “in/on water directed transition‐metal‐catalysis”, though still underdeveloped, appeared one prominent themes in sustainable organic chemistry. This article covers advancements, mechanistic insights and application (hetero)arenes in/on presence transition‐metal‐catalysis.

Language: Английский

Citations

7
Synthesis of C5-boryl indoles via a borane-catalyzed borylation/hydride transfer cascade DOI
Baoquan Zhan,

Jianxing Lv,

Jiangyue Wu

et al.

Chem Catalysis, Journal Year: 2024, Volume and Issue: 4(5), P. 100975 - 100975

Published: April 15, 2024

Language: Английский

Citations

2
Metal‐Catalyzed Coupling of N‐Tosylhydrazones with Compounds Containing C‐H/Heteroatom‐H Bonds DOI

Akanksha Akanksha,

Ajaya Kumar Singh,

Anupama Asthana

et al.

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 16, 2024

Abstract The present review covers various advances in the field of metal‐catalyzed coupling N ‐tosylhydrazones with compounds containing C−H/heteroatom‐H bonds, including transition metal catalysts i. e., Pd, Rh, Cu, Ag, Ni and Co resulting alkylated, alkenylated, alkynylated, allenylated, annulated many other products. A carbene migratory insertion process play a key role carbon‐carbon single bond (C−C) double (C=C) formation undergoes variety cascade reactions to synthesize wide scope pharmaceutically medicinally valuable scaffoldings.

Language: Английский

Citations

1