Boron-Mediated Selective C–H Hydroxylation of 1-Phenyl-1H-Pyrazoles DOI
Gaorong Wu, Yu-xi Liu, Weiming Chen

et al.

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

Published: Nov. 8, 2024

A novel strategy for boron-mediated C-H hydroxylation of 1-phenyl-1

Language: Английский

BX3-mediated borylation for the synthesis of organoboron compounds DOI
Chunhua Yang

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(23), P. 6010 - 6020

Published: Jan. 1, 2023

This review summarizes the recent progress in borylation driven by BX 3 fields of organic synthesis and drug synthesis.

Language: Английский

Citations

10
Electron-Deficient CpRh(III)-Catalyzed C–H Functionalization of N-2-Pyridylanilines: Branch-Selective Alkenylation with Alkenes and Annulation with Alkynes DOI

Wataru Hosoya,

Daisuke Yokose,

Ken Tanaka

et al.

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

Published: March 20, 2025

We report the electron-deficient CpRh(III) [CpERh(III)] complex-catalyzed branch selective alkenylation with aliphatic alkenes and annulation internal alkynes using N-2-pyridylanilines. In these reactions, CpERh(III) catalyst is more active than electron-rich Cp*Rh(III) catalyst, used commonly in C–H activation, reactions proceed a catalytic amount of Cu(II) oxidant under air at lower temperatures conventional methods. From mechanistic considerations, steric repulsion between ligand directing group may be responsible for alkenylation.

Language: Английский

Citations

0
BBr3-Mediated ortho C–H Borylation of Benzamides DOI
Yixuan Liang,

Chengyu Du,

C. Dong

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 25, 2025

We have developed a BBr3-mediated, metal-free ortho C-H borylation of benzamides, enabling the synthesis wide range ortho-borylated benzamides in moderate to good yields. This transformation offers convenient strategy for accessing functionalized which are valuable intermediates pharmaceuticals, agrochemicals, and fine chemical synthesis.

Language: Английский

Citations

0
Metal-free directed C−H borylation of 2-(N-methylanilino)-5-fluoropyridines and 2-benzyl-5-fluoropyridines DOI
Gaorong Wu, Xiaobo Xu, Shuai Wang

et al.

Chinese Chemical Letters, Journal Year: 2021, Volume and Issue: 33(4), P. 2005 - 2008

Published: Sept. 30, 2021

Language: Английский

Citations

22
Metal‐Free Directed Site‐Selective Csp3‐H Borylation of Saturated Cyclic Amines DOI Creative Commons
Puneeth Kumar Someswara Ashwathappa, Takuya Higashi, Vincent Desrosiers

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(39)

Published: Aug. 3, 2023

The borylation of Csp3 -H bonds is a challenging transformation that typically restricted to transition metal catalysis. Herein, we report the site-selective metal-free saturated cyclic amines. It possible selectively borylate piperidine derivatives at α or β positions according reaction conditions. mechanism was supported by NMR spectroscopy, calorimetry experiments and density functional theory (DFT) computations. suggests dehydrogenated complexation with BBr3 produce an enamine intermediate, which in turn borylated either position

Language: Английский

Citations

9
Directing group controlled regioselective C–H borylation of 2-arylphenolic compounds at room temperature DOI

Jiao Kang,

Jing Liu, Zhilong Chen

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(15), P. 4249 - 4257

Published: Jan. 1, 2024

The Fe(OTf) 3 -promoted directing group-controlled regioselective C–H borylation of 2-arylarenolic compounds was achieved at room temperature, affording two useful arylboronic acids efficiently.

Language: Английский

Citations

3
Regioselective Transition‐Metal‐Free Arene C−H Borylations: From Directing Groups to Borylation Template Reagents DOI
Guillaume Berionni

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 61(40)

Published: Aug. 26, 2022

Abstract The latest developments in the field of electrophilic C−H borylation reactions arenes and heteroarenes without transition metals are briefly overviewed, with a particular emphasis on advances enabling highly regioselective borylations indoles indolines using template reagents.

Language: Английский

Citations

14
Regioselective ortho halogenation of N-aryl amides and ureas via oxidative halodeboronation: harnessing boron reactivity for efficient C–halogen bond installation DOI Creative Commons

Ganesh Shinde,

Ganesh S. Ghotekar, Francoise M. Amombo Noa

et al.

Chemical Science, Journal Year: 2023, Volume and Issue: 14(46), P. 13429 - 13436

Published: Jan. 1, 2023

The installation of the C-halogen bond at ortho position N-aryl amides and ureas represents a tool to prepare motifs that are ubiquitous in biologically active compounds. To construct such prevalent bonds, most methods require use precious metals multistep process. Here we report novel protocol for long-standing challenge regioselective halogenation using an oxidative halodeboronation. By harnessing reactivity boron over nitrogen, merge carbonyl-directed borylation with consecutive halodeboronation, enabling precise introduction C-X desired ureas. This method offers efficient, practical, scalable solution synthesizing halogenated N-heteroarenes under mild conditions, highlighting superiority directing regioselectivity reaction.

Language: Английский

Citations

8
Metal-free Borylation of α-Naphthamides and Phenylacetic Acid Drug DOI Creative Commons
Suman Maji, Parveen Rawal, Animesh Ghosh

et al.

JACS Au, Journal Year: 2024, Volume and Issue: 4(9), P. 3679 - 3689

Published: Sept. 11, 2024

Site-selective C-H borylation is an important strategy for constructing molecular diversity in arenes and heteroarenes. Although transition-metal-catalyzed well explored, developing metal-free strategies remains scarce. Herein, we developed a straightforward approach BBr

Language: Английский

Citations

2
Metal‐free sp2‐C7−H Borylation of Tryptophan Containing Peptides and Late‐stage Modification DOI

Rachana Meena,

Shashank Shekhar,

Shabina B. Ansari

et al.

Chemistry - An Asian Journal, Journal Year: 2023, Volume and Issue: 18(23)

Published: Oct. 17, 2023

The discovery of milder and robust strategies to enable the introduction organoboronates in peptides remains conspicuously underdeveloped. Herein, we demonstrate an efficient method for site-selective sp2 -C7-H borylation tryptophan under metal-free condition using BBr3 directed by pivaloyl group. versatility this approach is that gram scale synthesis C7-borylated N-Phth-Trp(N-Piv)(C7-BPin)-OMe was modified into various C7-substituted derivatives. Moreover, strategy enables peptide elongation late-stage peptides, natural product Brevianamide F drug Oglufanide.

Language: Английский

Citations

6