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

и другие.

Chemistry - A European Journal, Год журнала: 2024, Номер 31(8)

Опубликована: Ноя. 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.

Язык: Английский

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

Chengyu Du,

C. Dong

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Апрель 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.

Язык: Английский

Процитировано

0
Metal-free Borylation of α-Naphthamides and Phenylacetic Acid Drug DOI Creative Commons
Suman Maji, Parveen Rawal, Animesh Ghosh

и другие.

JACS Au, Год журнала: 2024, Номер 4(9), С. 3679 - 3689

Опубликована: Сен. 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

Язык: Английский

Процитировано

2
Boron-Mediated Selective C–H Hydroxylation of 1-Phenyl-1H-Pyrazoles DOI
Gaorong Wu, Yu-xi Liu, Weiming Chen

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 8, 2024

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

Язык: Английский

Процитировано

1
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

и другие.

Chemistry - A European Journal, Год журнала: 2024, Номер 31(8)

Опубликована: Ноя. 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.

Язык: Английский

Процитировано

1