Visible-Light-Induced C(sp2)―P Cross-Coupling Reactions Catalyzed by Boron Carbonitride

被引：0

作者：

Wang, Rong ^{[1
]}

Liu, Xin ^{[1
]}

Hou, Hao ^{[1
]}

Zheng, Meifang ^{[1
]}

机构：

[1] Fuzhou Univ, Coll Chem, State Key Lab Photocatalysis Energy & Environm, Fuzhou 350116, Peoples R China

来源：

CHEMCATCHEM | 2025年 / 17卷 / 05期

基金：

中国国家自然科学基金;

关键词：

Boron carbonitride; C(sp(2))& horbar; P cross-coupling; Heterogeneous photocatalysis; Radical; Visible light; LIGANDS; ACIDS; ARYL;

D O I：

暂无

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A visible-light-induced protocol has been developed for the construction of C(sp(2))& horbar;P bonds with heterogeneous boron carbonitrides (BCN). The system features with broad scope and mild reaction conditions, providing various aryl phosphates in moderate to good yields from arenes and aryl halides. Mechanism studies verify a radical process, and C & horbar;H bond cleavage is not involved in the rate-determined step. Furthermore, the strategy allows the late-stage phosphonation of biologically active compounds and facilitates gram-scale synthesis, which offers a metal-free arene for valuable phosphorus-containing compounds.

引用

页数：6

共 28 条

[1] Phosphorus Lewis acids: emerging reactivity and applications in catalysis [J].

Bayne, J. M. ;

Stephan, D. W. .

CHEMICAL SOCIETY REVIEWS, 2016, 45 (04) :765-774

[2] Highly Stereoselective Synthesis of 2,2-Disubstituted Vinylphosphonates via Aryl to Vinyl 1,4-Palladium Migration [J].

Chen, Yan-Zhen ;

Bao, Geng-Yu ;

Zhan, Xin-Chen ;

Fu, Jian-Guo ;

Ji, Xiao-Ming ;

Zhang, Shu-Sheng ;

Feng, Chen-Guo .

CHINESE JOURNAL OF CHEMISTRY, 2022, 40 (18) :2188-2192

[3] Selected organophosphorus compounds with biological activity. Applications in medicine [J].

Demkowicz, Sebastian ;

Rachon, Janusz ;

Dasko, Mateusz ;

Kozak, Witold .

RSC ADVANCES, 2016, 6 (09) :7101-7112

[4] Palladium-Catalyzed Phosphorylation of Aryl Mesylates and Tosylates [J].

Fu, Wai Chung ;

So, Chau Ming ;

Kwong, Fuk Yee .

ORGANIC LETTERS, 2015, 17 (23) :5906-5909

[5] Heterogeneous Single-Atom Photocatalysts: Fundamentals and Applications [J].

Gao, Chao ;

Low, Jingxiang ;

Long, Ran ;

Kong, Tingting ;

Zhu, Junfa ;

Xiong, Yujie .

CHEMICAL REVIEWS, 2020, 120 (21) :12175-12216

[6] Organic semiconductor photocatalyst can bifunctionalize arenes and heteroarenes [J].

Ghosh, Indrajit ;

Khamrai, Jagadish ;

Savateev, Aleksandr ;

Shlapakov, Nikita ;

Antonietti, Markus ;

Koenig, Burkhard .

SCIENCE, 2019, 365 (6451) :360-+

[7] Super-Reducing Behavior of Benzo[b]phenothiazine Anion Under Visible-Light Photoredox Condition [J].

Halder, Supriya ;

Mandal, Sourav ;

Kundu, Abhishek ;

Mandal, Baishanal ;

Adhikari, Debashis .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 145 (41) :22403-22412

[8] Microwave-Assisted Palladium Acetate-Catalyzed C-P Cross-Coupling of Arylboronic Acids and >P(O)H Reagents in the Absence of the Usual Mono- and Bidentate P-Ligands: Mechanistic Insights [J].

Huszar, Bianka ;

Mucsi, Zoltan ;

Keglevich, Gyorgy .

JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (16) :11980-11991

[9] Microwave-Assisted Palladium-Catalyzed Cross-Coupling of Aryl and Vinyl Halides with H-Phosphonate Diesters [J].

Kalek, Marcin ;

Ziadi, Asraa ;

Stawinski, Jacek .

ORGANIC LETTERS, 2008, 10 (20) :4637-4640

[10] Preparation of Arylphosphonates by Palladium(0)-Catalyzed Cross-Coupling in the Presence of Acetate Additives: Synthetic and Mechanistic Studies [J].

Kalek, Marcin ;

Jezowska, Martina ;

Stawinski, Jacek .

ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (18) :3207-3216

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