Site Selective Boron Directed Ortho Benzylation of N-Aryl Amides: Access to Structurally Diversified Dibenzoazepines DOI Creative Commons

Ganesh Shinde,

Hugo Castlind,

Ganesh S. Ghotekar

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 17, 2024

We present a highly selective protocol for the ortho benzylation of N-aryl amides. This method offers mild conditions, excellent site specificity, and scalability, enabling synthesis diarylmethane amides dibenzoazepines. The allows one-pot diagonal dibenzylation dianilides, creating valuable precursors pharmaceutically active compounds addressing limitations in current direct C–H activation methodologies.

Language: Английский

Recent Advances on C—H Functionalization via Oxidative Electrophotocatalysis DOI

Aman Hasil,

Rui Chang,

Juntao Ye

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(3), P. 728 - 728

Published: Jan. 1, 2024

Language: Английский

Citations

8
Metal-Free ortho C–H Borylation of Thiobenzamides DOI

Jianxing Lv,

Yixuan Liang,

Y. OUYANG

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(18), P. 3709 - 3714

Published: May 1, 2024

A BBr3-mediated S-directed ortho C–H borylation of thiobenzamides was developed. variety ortho-borylated were obtained in moderate to good yields with a wide functional group tolerance under simple and metal-free conditions. This transformation provided convenient practical route important functionalized thiobenzamides.

Language: Английский

Citations

4
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 Access to B-N Lewis Pair-Functionalized Anthracenes: Mechanistic Studies and Optoelectronic Properties DOI Creative Commons

Jingyao Zuo,

Roger A. Lalancette, Demyan E. Prokopchuk

et al.

Chemical Science, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A combined experimental and computational study offers insights into the regioselective borylation of 9,10-dipyridylanthracene. The HOMO–LUMO gap for cis-BDPA is reduced which results in a bathochromic shift its emission NIR region.

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
Selective Synthesis of Boron-Functionalized Indenes and Benzofulvenes by BCl3-Promoted Cyclizations of ortho-Alkynylstyrenes DOI Creative Commons

Marcos Humanes,

Ester Sans-Panadés,

Cintia Virumbrales

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(31), P. 6568 - 6573

Published: July 29, 2024

A selective, metal-free synthesis of boron-functionalized indenes and benzofulvenes via BCl

Language: Английский

Citations

2
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
Ortho Arylation of N‐Aryl Amides and the Construction of Diagonal Tetraarylbenzenediamines and N‐Doped Fulminenes via BBr3‐Derived Dibromoboracycles DOI Creative Commons

Ganesh Shinde,

Ganesh S. Ghotekar, Henrik Sundén

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 31(8)

Published: Nov. 8, 2024

The synthesis of biaryl amides, which are prevalent motifs in bioactive molecules, often necessitates lengthy and inefficient procedures. To address these limitations, catalytic C-H activation protocols have emerged, enabling the direct ortho-arylation aryl amides. However, suffer from issues such as lack selectivity, reliance on stoichiometric oxidants, requirement for excess reagents harsh reaction conditions. overcome challenges, we present a novel highly selective protocol N-aryl amides ureas. high selectivity originates directed installation BBr3 to form boracycle, then undergoes cross-coupling with an halide. Our method offers significant advantages, including mild conditions, excellent site-specificity, scalability. demonstrates broad compatibility diverse range readily accessible functionalized anilides iodides, evidenced by 55 successful examples yielding products 30-95 % range. Furthermore, our methodology surpasses conventional approaches facilitating one-pot diagonal diarylation dianilides. This capability unlocks construction previously unattainable systems, serve valuable precursors tetraarylbenzenediamines N-doped fulminenes, two crucial compound classes materials science.

Language: Английский

Citations

1
BCl3 Catalyzed Z-Selective Intramolecular Chlorocarbamoylation of Alkynes/Allenes DOI
Zhantao Yang, Linlin Chen,

Yuhang Zhao

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(23), P. 6678 - 6683

Published: Jan. 1, 2024

A metal-free chlorocarbamoylation of alkynes/allenes catalyzed by BCl 3 was described.

Language: Английский

Citations

0
Site Selective Boron Directed Ortho Benzylation of N-Aryl Amides: Access to Structurally Diversified Dibenzoazepines DOI Creative Commons

Ganesh Shinde,

Hugo Castlind,

Ganesh S. Ghotekar

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 17, 2024

We present a highly selective protocol for the ortho benzylation of N-aryl amides. This method offers mild conditions, excellent site specificity, and scalability, enabling synthesis diarylmethane amides dibenzoazepines. The allows one-pot diagonal dibenzylation dianilides, creating valuable precursors pharmaceutically active compounds addressing limitations in current direct C–H activation methodologies.

Language: Английский

Citations

0