TBHP/TFA mediated oxidative cross-dehydrogenative coupling of N-heterocycles with aldehydes

被引:58
作者
Chen, Jiayu [1 ,2 ]
Wan, Miao [1 ]
Hua, Jing [3 ]
Sun, Yi [1 ,2 ]
Lv, Zheng [2 ]
Li, Wei [2 ]
Liu, Lei [1 ,3 ]
机构
[1] Sch Pharmaceut Sci, Jinan 250012, Peoples R China
[2] Shandong Univ Tradit Chinese Med, Sch Pharm, Dept Pharmaceut Anal, Jinan 250355, Shandong, Peoples R China
[3] Guangxi Normal Univ, Minist Educ China, Key Lab Chem & Mol Engn Med Resources, Guilin 541004, Peoples R China
基金
美国国家科学基金会;
关键词
C-H BONDS; STRUCTURALLY DIVERSE; TERTIARY-AMINES; TOLUENE DERIVATIVES; CATALYZED SYNTHESIS; METHYL ARENES; ACTIVATION; C(SP(3))-H; SP(3); ALKYLATION;
D O I
10.1039/c5ob01763g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An effective and metal-free oxidative cross-dehydrogenative coupling (CDC) of N-heterocycles with diverse aldehydes has been established in the presence of TBHP/TFA. The scope with respect to aldehyde and N-heterocycle components is broad, allowing facile synthesis of a broad range of structurally diverse C-1-acyl substituted heterocycles in good efficiency.
引用
收藏
页码:11561 / 11566
页数:6
相关论文
共 72 条
[1]   Ni(II)-Catalyzed Oxidative Coupling between C(sp2)-H in Benzamides and C(sp3)-H in Toluene Derivatives [J].
Aihara, Yoshinori ;
Tobisu, Mamoru ;
Fukumoto, Yoshiya ;
Chatani, Naoto .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (44) :15509-15512
[2]   Regiospecific Benzoylation of Electron-Deficient N-Heterocycles with Methylbenzenes via a Minisci-Type Reaction [J].
Ali, Wajid ;
Behera, Ahalya ;
Guin, Srimanta ;
Patel, Bhisma K. .
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (11) :5625-5632
[3]   Copper-catalyzed oxidative sp3 C-H bond arylation with aryl boronic acids [J].
Basle, Olivier ;
Li, Chao-Jun .
ORGANIC LETTERS, 2008, 10 (17) :3661-3663
[4]   Catalytic stereoselective benzylic C-H functionalizations by oxidative C-H activation and organocatalysis [J].
Benfatti, Fides ;
Capdevila, Montse Guiteras ;
Zoli, Luca ;
Benedetto, Elena ;
Cozzi, Pier Giorgio .
CHEMICAL COMMUNICATIONS, 2009, (39) :5919-5921
[5]  
Bergonzini G, 2014, CHEM SCI, V5, P112, DOI [10.1039/c3sc52265b, 10.1039/C3SC52265B]
[6]   Efficient copper-catalyzed benzylic amidation with anhydrous chloramine-T [J].
Bhuyan, Ranjana ;
Nicholas, Kenneth M. .
ORGANIC LETTERS, 2007, 9 (20) :3957-3959
[7]   Mechanistic Studies on a Cu-Catalyzed Aerobic Oxidative Coupling Reaction with N-Phenyl Tetrahydroisoquinoline: Structure of Intermediates and the Role of Methanol As a Solvent [J].
Boess, Esther ;
Sureshkumar, Devarajulu ;
Sud, Abhishek ;
Wirtz, Cornelia ;
Fares, Christophe ;
Klussmann, Martin .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (21) :8106-8109
[8]   Discovery of a series of nonpeptide small molecules that inhibit the binding of insulin-like growth factor (IGF) to IGF-binding proteins [J].
Chen, C ;
Zhu, YF ;
Liu, XJ ;
Lu, ZX ;
Xie, Q ;
Ling, N .
JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (23) :4001-4010
[9]   Direct Condensation of Sulfonamide and Formamide: Nal-Catalyzed Synthesis of N-Sulfonyl Formamidine Using TBHP as Oxidant [J].
Chen, Shulin ;
Xu, Yuan ;
Wan, Xiaobing .
ORGANIC LETTERS, 2011, 13 (23) :6152-6155
[10]   Structurally Diverse α-Substituted Benzopyran Synthesis through a Practical Metal-Free C(sp3)-H Functionalization [J].
Chen, Wenfang ;
Xie, Zhiyu ;
Zheng, Hongbo ;
Lou, Hongxiang ;
Liu, Lei .
ORGANIC LETTERS, 2014, 16 (22) :5988-5991