Electrochemical Oxidative C-C Bond Cleavage of Ketones for C-N Bond Formation: A Route to Amides

被引：17

作者：

He, Yonghui ^{[1
,2
]}

Zeng, Liang ^{[1
,2
]}

Li, Ming ^{[1
,2
]}

Gu, Lijun ^{[1
,2
,3
]}

Zhang, Shengyong ^{[1
,2
]}

Li, Ganpeng ^{[1
,2
]}

机构：

[1] Yunnan Minzu Univ, Key Lab Chem Ethn Med Resources, State Ethn Affairs Commiss, Kunming 650500, Yunnan, Peoples R China

[2] Yunnan Minzu Univ, Minist Educ, Kunming 650500, Yunnan, Peoples R China

[3] Guizhou Univ, Key Lab Green Pesticide & Agr Bioengn, Minist Educ, Guiyang 550025, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 19期

基金：

中国国家自然科学基金;

关键词：

METHYL KETONES; METAL-FREE; DIRECT TRANSFORMATION; OXYGENATION; ALDEHYDES;

D O I：

10.1021/acs.joc.2c01025

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, we report an efficient electrochemical activation of the C-C bond of aryl ketones for the preparation of amides under catalyst-and external-oxidant-free conditions using aliphatic amines as the N source. Under environmentally benign electrolysis conditions, a series of amides were synthesized in good yield. Our control experiments revealed that electricity plays an important role in this transformation.

引用

页码：12622 / 12631

页数：10

共 50 条

[21] Serendipitous Synthesis of Pyridoquinazolinones via an Oxidative C-C Bond Cleavage
Brendel, Matthias
Sakhare, Priyanka R.
Dahiya, Gaurav
Subramanian, Parthasarathi
Kaliappan, Krishna P.
JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (12) : 8102 - 8110
[22] Base-catalyzed synthesis of amides and imines via C-C and C=C bond cleavage
Yadav, Dilip Kumar T.
Bhanage, Bhalchandra M.
RSC ADVANCES, 2015, 5 (16) : 12387 - 12391
[23] From amides to urea derivatives or carbamates with chemospecific C-C bond cleavage at room temperature
Lv, Cong
Liu, Dan
Muschin, Tegshi
Bai, Chaolumen
Bao, Agula
Bao, Yong-Sheng
ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (05) : 1354 - 1363
[24] Iodine-catalyzed oxidative C-C bond cleavage for benzoic acids and benzamides from alkyl aryl ketones
Sathyanarayana, Pochampalli
Upare, Atul
Ravi, Owk
Muktapuram, Prathap Reddy
Bathula, Surendar Reddy
RSC ADVANCES, 2016, 6 (27) : 22749 - 22753
[25] KMnO4-mediated oxidative C-N bond cleavage of tertiary amines: Synthesis of amides and sulfonamides
Zhang, Zhang
Liu, Yong-Hong
Zhang, Xi
Wang, Xi-Cun
TETRAHEDRON, 2019, 75 (19) : 2763 - 2770
[26] Cu(II)-promoted oxidative C-N bond cleavage of N-benzoylamino acids to primary aryl amides
Zhou, Liandi
Liu, Wei
Zhao, Yongli
Chen, Junmin
ARKIVOC, 2016, : 52 - 62
[27] Developments towards synthesis of N-heterocycles from amidines via C-N/C-C bond formation
Guo, Wei
Zhao, Mingming
Tan, Wen
Zheng, Lvyin
Tao, Kailiang
Fan, Xiaolin
ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (13) : 2120 - 2141
[28] Photocatalytic, Oxidative Cleavage of C-C Bond in Lignin Models and Native Lignin
Xu, Enjie
Xie, Fuyu
Liu, Tianwei
He, Jianghua
Zhang, Yuetao
CHEMISTRY-A EUROPEAN JOURNAL, 2024, 30 (24)
[29] New Electrophilic Addition of α-Diazoesters with Ketones for Enantioselective C-N Bond Formation
Li, Wei
Liu, Xiaohua
Hao, Xiaoyu
Hu, Xiaolei
Chu, Yangyang
Cao, Weidi
Qin, Song
Hu, Changwei
Lin, Lili
Feng, Xiaoming
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (39) : 15268 - 15271
[30] Aminotetrazole Synthesis from Secondary Amides by C-C Bond Nitrogenation
Zhang, Cheng
Liu, Jianzhong
Cheng, Zengrui
Li, Junhua
Song, Song
Jiao, Ning
SYNLETT, 2023, 34 (12) : 1534 - 1538

← 1 2 3 4 5 →