Palladium-Catalyzed C(sp2)-H Acetoxylation via Electrochemical Oxidation

被引:118
作者
Li, Yi-Qian [1 ,2 ]
Yang, Q-Liang [2 ]
Fang, Ping [2 ]
Mei, Tian-Sheng [2 ]
Zhang, Dayong [1 ]
机构
[1] China Pharmaceut Univ, Inst Pharmaceut Sci, Nanjing, Jiangsu, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China
关键词
C-H ACETOXYLATION; FORMING REDUCTIVE ELIMINATION; DIRECTING-GROUP; UNACTIVATED C(SP(3))-H; FUNCTIONALIZATION; OXYGENATION; BONDS; ACID; HYDROXYLATION; COMPLEXES;
D O I
10.1021/acs.orglett.7b01138
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Palladium-catalyzed arene C(sp2)H acetoxylation has emerged as a powerful tool to construct a carbonoxygen (CO) bond. However, the requirement of stoichiometric chemical oxidants for this transformation possesses a significant disadvantage. To solve this fundamental problem, we now report an anodic oxidation strategy to achieve arene C(sp(2))H acetoxylation.
引用
收藏
页码:2905 / 2908
页数:4
相关论文
共 87 条
[1]   Catalytic Electrochemical C-H Iodination and One-Pot Arylation by ON/OFF Switching of Electric Current [J].
Aiso, Hiroko ;
Kochi, Takuya ;
Mutsutani, Hitoshi ;
Tanabe, Takamasa ;
Nishiyama, Shigeru ;
Kakiuchi, Fumitoshi .
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (17) :7718-7724
[2]   Electrochemical recycling of benzoquinone in the Pd/benzoquinone-catalyzed Heck-type reactions from arenes [J].
Amatore, Christian ;
Cammoun, Chama ;
Jutand, Anny .
ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (03) :292-296
[3]   Cooperative electrocatalytic alcohol oxidation with electron-proton-transfer mediators [J].
Badalyan, Artavazd ;
Stahl, Shannon S. .
NATURE, 2016, 535 (7612) :406-410
[4]   THE OXIDATIVE ADDITION OF IODOMETHANE TO [PDME2(2,2'-BIPYRIDYL)] AND THE X-RAY STRUCTURE OF THE ORGANOPALLADIUM(IV) PRODUCT FAC-[PDME3(2,2'-BIPYRIDYL)L] [J].
BYERS, PK ;
CANTY, AJ ;
SKELTON, BW ;
WHITE, AH .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (23) :1722-1724
[5]  
Camasso NM, 2014, J AM CHEM SOC, V136, P12771, DOI [10.1021/Ja507056u, 10.1021/ja507056u]
[6]   Pd(II)-catalyzed alkoxylation of unactivated C(sp3)-H and C(sp2)-H bonds using a removable directing group: efficient synthesis of alkyl ethers [J].
Chen, Fa-Jie ;
Zhao, Sheng ;
Hu, Fang ;
Chen, Kai ;
Zhang, Qi ;
Zhang, Shuo-Qing ;
Shi, Bing-Feng .
CHEMICAL SCIENCE, 2013, 4 (11) :4187-4192
[7]   Electrocatalytic Aziridination of Alkenes Mediated by n-Bu4NI: A Radical Pathway [J].
Chen, Jie ;
Yan, Wei-Qing ;
Lam, Chiu Marco ;
Zeng, Cheng-Chu ;
Hu, Li-Ming ;
Little, R. Daniel .
ORGANIC LETTERS, 2015, 17 (04) :986-989
[8]   Pd(II)-Catalyzed Enantioselective C-H Activation/C-O Bond Formation: Synthesis of Chiral Benzofuranones [J].
Cheng, Xiu-Fen ;
Li, Yan ;
Su, Yi-Ming ;
Yin, Feng ;
Wang, Jian-Yong ;
Sheng, Jie ;
Vora, Harit U. ;
Wang, Xi-Sheng ;
Yu, Jin-Quan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (04) :1236-1239
[9]   PyDipSi: A General and Easily Modifiable/Traceless Si-Tethered Directing Group for C-H Acyloxylation of Arenes [J].
Chernyak, Natalia ;
Dudnik, Alexander S. ;
Huang, Chunhui ;
Gevorgyan, Vladimir .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (24) :8270-+
[10]   Palladium-Catalyzed ortho-CH-Bond Oxygenation of Aromatic Ketones [J].
Choy, Pui Ying ;
Kwong, Fuk Yee .
ORGANIC LETTERS, 2013, 15 (02) :270-273