A carboxylate-assisted amination/unactivated C(sp2)-H arylation reaction via a palladium/norbornene cooperative catalysis

被引:24
作者
An, Yang [1 ]
Zhang, Bo-Sheng [1 ]
Zhang, Zhe [1 ]
Liu, Ce [1 ]
Gou, Xue-Ya [1 ]
Ding, Ya-Nan [1 ]
Liang, Yong-Min [1 ]
机构
[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
基金
中国国家自然科学基金;
关键词
INTRAMOLECULAR ALKANE ARYLATION; C-H FUNCTIONALIZATION; PHENANTHRIDINE DERIVATIVES; OXIDATIVE CYCLIZATION; ARYL IODIDES; METAL-FREE; BOND; CONSTITUENTS; ALKALOIDS; AMINATION;
D O I
10.1039/c9cc09265j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This report describes a carboxylate-assisted palladium-catalysed Catellani reaction, which is compatible with ortho-amination and unactivated C(sp(2))-H arylation. This method was used to synthesize a series of 1-amino substituted dihydrophenanthridines, phenanthridines and 6H-benzo[c]chromenes. Based on kinetic isotope experiments, the kinetic curve proves that pivalic acid accelerates the reaction rate of unactivated C(sp(2))-H activation, and thus this rate can keep up with the five membered aryl-norbornene-palladacycle (ANP) intermediate.
引用
收藏
页码:5933 / 5936
页数:4
相关论文
共 71 条
[1]   2 BETAINE-TYPE ALKALOIDS FROM EGYPTIAN PANCRATIUM-MARITIMUM [J].
ABOUDONIA, AH ;
ABIB, AA ;
ELDIN, AS ;
EVIDENTE, A ;
GABER, M ;
SCOPA, A .
PHYTOCHEMISTRY, 1992, 31 (06) :2139-2141
[2]  
Ackermann L, 2009, MODERN ARYLATION METHODS, P1
[3]   Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].
Ackermann, Lutz .
CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345
[4]   Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].
Ackermann, Lutz ;
Vicente, Ruben ;
Kapdi, Anant R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9792-9826
[5]   OXOCRININE AND OTHER ALKALOIDS FROM CRINUM-AMERICANUM [J].
ALI, AA ;
ELSAYED, HM ;
ABDALLAH, OM ;
STEGLICH, W .
PHYTOCHEMISTRY, 1986, 25 (10) :2399-2401
[6]   New light-induced iminyl radical cyclization reactions of acyloximes to isoquinolines [J].
Alonso, Rafael ;
Campos, Pedro J. ;
Garcia, Barbara ;
Rodriguez, Miguel A. .
ORGANIC LETTERS, 2006, 8 (16) :3521-3523
[7]   Photochemical study of tris(benzotriazol-1-yl)methane [J].
Androsov, Dmitry A. ;
Neckers, Douglas C. .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (04) :1148-1152
[8]   Formal Synthesis of Nitidine and Nk109 via Palladium-Catalyzed Domino Direct Arylation/N-Arylation of Aryl Triflates [J].
Blanchot, Mathieu ;
Candito, David A. ;
Larnaud, Florent ;
Lautens, Mark .
ORGANIC LETTERS, 2011, 13 (06) :1486-1489
[9]   CONSTITUENTS OF ZANTHOXYLUM .6. SOME ALKALOIDS AND OTHER CONSTITUENTS OF ZANTHOXYLUM-MICROCARPUM AND ZANTHOXYLUM-PROCERUM [J].
BOULWARE, RT ;
STERMITZ, FR .
JOURNAL OF NATURAL PRODUCTS, 1981, 44 (02) :200-205
[10]   A route to annulated indoles via a palladium-catalyzed tandem alkylation/direct arylation reaction [J].
Bressy, C ;
Alberico, D ;
Lautens, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (38) :13148-13149