Selective C-C Bond Cleavage of Cycloalkanones by NaNO2/HCl

被引：7

作者：

He, Tianyu ^{[1
]}

Chen, Dengfeng ^{[1
]}

Qian, Shencheng ^{[1
]}

Zheng, Yu ^{[1
]}

Huang, Shenlin ^{[1
]}

机构：

[1] Nanjing Forestry Univ, Jiangsu Coinnovat Ctr Efficient Proc & Utilizat F, Int Innovat Ctr Forest Chem & Mat, Coll Chem Engn, Nanjing 210037, Jiangsu, Peoples R China

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 16期

基金：

中国博士后科学基金;

关键词：

SODIUM-NITRITE; KETONES; ACTIVATION; OXIDATION;

D O I：

10.1021/acs.orglett.1c02327

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel selective fragmentation of cycloalkanones by NaNO2/HCl has been established. The C-C bond cleavage reaction proceeds smoothly under mild conditions, selectively affording versatile keto acids or oxime acids. The methodology can streamline the synthesis of valuable chiral molecules and isocoumarins from readily available feedstocks.

引用

页码：6525 / 6529

页数：5

共 50 条

[41] Oxidative C-C bond cleavage of lignin via electrocatalysis
Huang, Jinshu
Jian, Yumei
Zhou, Min
Wu, Hongguo
FRONTIERS IN CHEMISTRY, 2022, 10
[42] Homolytic cleavage C-C bond in the electrooxidation of ethanol and bioethanol
Barroso, J.
Pierna, A. R.
Blanco, T. C.
Morallon, E.
Huerta, F.
JOURNAL OF POWER SOURCES, 2011, 196 (09) : 4193 - 4199
[43] Aromatic C-C Bond Cleavage in a Curved π-System of Aminocorannulene
Guo, Weijie
Ding, Wanjian
Yao, Yuqing
Rajca, Suchada
Li, Qiaolian
Jiang, Hua
Rajca, Andrzej
Wang, Ying
ORGANIC LETTERS, 2023, 25 (21) : 3972 - 3977
[44] Reductase of Mutanobactin Synthetase Triggers Sequential C-C Macrocyclization, C-S Bond Formation, and C-C Bond Cleavage
Wang, Min
Xie, Zhoujie
Tang, Shoubin
Chang, Ee Ling
Tang, Yue
Guo, Zhengyan
Cui, Yinglu
Wu, Bian
Ye, Tao
Chen, Yihua
ORGANIC LETTERS, 2020, 22 (03) : 960 - 964
[45] Ring Opening of Methylenecycloalkenes via the C-C Bond Cleavage
Necas, David
Kotora, Martin
ORGANIC LETTERS, 2008, 10 (22) : 5261 - 5263
[46] CLEAVAGE OF C-C BOND ACTIVATED BY H-ATOM
AMANO, A
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1979, (APR): : 104 - 104
[47] Mechanistic Insight into the Cleavage of an Aromatic C-C Bond by Tungsten
Li, Jun
Yoshizawa, Kazunari
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (03) : 783 - 787
[48] A simple entry into nido-C2B10 clusters:: HCl promoted cleavage of the C-C bond in ortho-carboranyl diphosphines
Charmant, Jonathan P. H.
Haddow, Mairi F.
Mistry, Rakesh
Norman, Nicholas C.
Orpen, A. Guy
Pringle, Paul G.
DALTON TRANSACTIONS, 2008, 11 (11) : 1409 - 1411
[49] CHEMISTRY OF ORGANOLANTHANOIDS - LANTHANOID-MEDIATED C-C BOND FORMATION AND CLEAVAGE AND C-C DOUBLE-BOND REDUCTION
HOU, ZM
FUJIWARA, Y
JINTOKU, T
MINE, N
YOKOO, K
TANIGUCHI, H
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (16): : 3524 - 3528
[50] Highly Selective Activation of C-H Bond and Inhibition of C-C Bond Cleavage by Tuning Strong Oxidative Pd Sites
Guo, Meng
Ma, Peijie
Wei, Lu
Wang, Jiayi
Wang, Zhiwei
Zheng, Kun
Cheng, Daojian
Liu, Yuxi
Dai, Hongxing
Guo, Guangsheng
Duan, Erhong
Deng, Jiguang
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 145 (20) : 11110 - 11120

← 1 2 3 4 5 →