Advances in Free-Radical Promoted C(sp3)-C(sp3) Bond Conversion

被引:9
作者
Wu Jintao [1 ]
Liu Zhongquan [1 ]
机构
[1] Nanjing Univ Chinese Med, Coll Pharm, Nanjing 210023, Peoples R China
基金
中国国家自然科学基金;
关键词
free-radical chemistry; C-C bond activation; photochemistry; electrochemistry; alcohol and ether; amine; aryl alkane; simple alkane; AEROBIC OXIDATIVE CLEAVAGE; BETA-KETO RADICALS; ARYLCYCLOPROPANE PHOTOCHEMISTRY; MOLECULAR-OXYGEN; 3+2 ANNULATION; ADIPIC ACID; METAL; ACTIVATION; FLUORINE; DERIVATIVES;
D O I
10.6023/cjoc202108043
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Efficient C-C bond conversion might bring innovation to clean energy and circular economy. In the past several decades, developments of relatively chemical active carbon-carbon multibond conversion have been made. However, the research progress on effective functionalization of inert C(sp(3))-C(sp(3)) bond is heavy going. The advances in this area from a free-radical chemistry point of view are summarized, which can help researchers who are interested in this topic to understand it quickly. The progesses as well as the corresponding mechanisms for free-radical promoted selective cleavage of saturated C-C bonds in alcohols and ethers, amines, aryl alkanes and simple alkancz are demonstrated. In each part, the explorations are depicted according to the initiating manners such as thermochemistry, photochemistry and electrochemistry.
引用
收藏
页码:16 / 32
页数:17
相关论文
共 105 条
[51]   Unexpected Copper-Catalyzed Aerobic Oxidative Cleavage of C(sp3)-C(sp3) Bond of Glycol Ethers [J].
Liu, Zhong-Quan ;
Zhao, Lixing ;
Shang, Xiaojie ;
Cui, Zili .
ORGANIC LETTERS, 2012, 14 (12) :3218-3221
[52]   Cobalt Nanoparticles-Catalyzed Widely Applicable Successive C-C Bond Cleavage in Alcohols to Access Esters [J].
Luo, Huihui ;
Wang, Lianyue ;
Shang, Sensen ;
Li, Guosong ;
Lv, Ying ;
Gao, Shuang ;
Dai, Wen .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (43) :19268-19274
[53]   Metal-Catalyzed Carbon-Carbon Bond Cleavage of Unstrained Alcohols [J].
Lutz, Marius D. R. ;
Morandi, Bill .
CHEMICAL REVIEWS, 2021, 121 (01) :300-326
[54]   Selective Carbon-Carbon Bond Cleavage for the Stereoselective Synthesis of Acyclic Systems [J].
Marek, Ilan ;
Masarwa, Ahmad ;
Delaye, Pierre-Olivier ;
Leibeling, Markus .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (02) :414-429
[55]   Metal-Free Synthesis of Adipic Acid via Organocatalytic Direct Oxidation of Cyclohexane under Ambient Temperature and Pressure [J].
Matsumoto, Yohei ;
Kuriyama, Masami ;
Yamamoto, Kosuke ;
Nishida, Koyo ;
Onomura, Osamu .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2018, 22 (09) :1312-1317
[56]   Selective Carbon-Carbon Bond Cleavage of Cyclopropanols [J].
McDonald, Tyler R. ;
Mills, L. Reginald ;
West, Michael S. ;
Rousseaux, Sophie A. L. .
CHEMICAL REVIEWS, 2021, 121 (01) :3-79
[57]   Reactions of transition metal-coordinated nitriles [J].
Michelin, RA ;
Mozzon, M ;
Bertani, R .
COORDINATION CHEMISTRY REVIEWS, 1996, 147 :299-338
[58]   Radical-Promoted C-C Bond Cleavage: A Deconstructive Approach for Selective Functionalization [J].
Morcillo, Sara P. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (40) :14044-14054
[59]   The Prowess of Photogenerated Amine Radical Cations in Cascade Reactions: From Carbocycles to Heterocycles [J].
Morris, Scott A. ;
Wang, Jiang ;
Zheng, Nan .
ACCOUNTS OF CHEMICAL RESEARCH, 2016, 49 (09) :1957-1968
[60]   Cleavage of Carbon-Carbon σ-Bonds of Four-Membered Rings [J].
Murakami, Masahiro ;
Ishida, Naoki .
CHEMICAL REVIEWS, 2021, 121 (01) :264-299