A palladium/norbornene cooperative catalysis to access N-containing bridged scaffolds

被引:30
作者
Gao, Qianwen [1 ]
Liu, Ze-Shui [1 ]
Hua, Yu [1 ]
Li, Lisha [1 ]
Cheng, Hong-Gang [1 ]
Cong, Hengjiang [1 ]
Zhou, Qianghui [1 ,2 ]
机构
[1] Wuhan Univ, Coll Chem & Mol Sci, Sauvage Ctr Mol Sci, Engn Res Ctr Organosilicon Cpds & Mat,Minist Educ, Wuhan 430072, Hubei, Peoples R China
[2] Wuhan Univ, Inst Adv Studies, Wuhan 430072, Hubei, Peoples R China
基金
中国国家自然科学基金; 中国博士后科学基金;
关键词
C-H FUNCTIONALIZATION; TETRASUBSTITUTED HELICAL ALKENES; ARYL IODIDES; AROMATIC FUNCTIONALIZATION; SEQUENTIAL REACTIONS; CATELLANI REACTION; ALPHA-ARYLATION; PALLADIUM; NORBORNENE; PD;
D O I
10.1039/c9cc03126j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A palladium/norbornene cooperative catalysis promoted annulation involving an ortho-C-H amination and intramolecular Heck cascade between aryl iodides and functionalized amination reagents is reported, thereby providing a highly convergent access to the unique N-containing bridged scaffolds: hexahydro-2,6-methano-1-benzazocine. The salient features of the reaction include its broad substrate scope (with respect to aryl iodides), its high step economy, and good chemoselectivity. Preliminary studies underscore the future promise of rendering this Catellani-type annulation enantioselective.
引用
收藏
页码:8816 / 8819
页数:4
相关论文
共 64 条
[1]   Palladium/Norbornene-Catalyzed C-H Alkylation/Alkyne Insertion/Indole Dearomatization Domino Reaction: Assembly of Spiroindolenine-Containing Pentacyclic Frameworks [J].
Bai, Lu ;
Liu, Jingjing ;
Hu, Wenjie ;
Li, Kunyu ;
Wang, Yaoyu ;
Luan, Xinjun .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (18) :5151-5155
[2]   Synthesis of 2-Azabicyclo[3.3.1]nonanes [J].
Bonjoch, Josep ;
Diaba, Faiza ;
Bradshaw, Ben .
SYNTHESIS-STUTTGART, 2011, (07) :993-1018
[3]   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
[4]  
Ca' N. D., 2008, ADV SYNTH CATAL, V350, P2513
[5]   Palladium-Catalyzed Domino Direct Arylation/N-Arylation: Convenient Synthesis of Phenanthridines [J].
Candito, David A. ;
Lautens, Mark .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (36) :6713-6716
[6]   Aryl transfer between Pd(II) centers or Pd(IV) intermediates in Pd-catalyzed domino reactions [J].
Cárdenas, DJ ;
Martín-Matute, B ;
Echavarren, AM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (15) :5033-5040
[7]  
Catellani M, 2005, TOP ORGANOMETAL CHEM, V14, P21
[8]   Palladium-catalyzed sequential reactions:: a new termination step leading to spirocyclohexadienone formation from p-iodophenol and bicyclo[2.2.1]heptene [J].
Catellani, M ;
Cugini, F ;
Bocelli, G .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 584 (01) :63-67
[9]   Catalytic Sequential Reactions Involving Palladacycle-Directed Aryl Coupling Steps [J].
Catellani, Marta ;
Motti, Elena ;
Della Ca, Nicola .
ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (11) :1512-1522
[10]   Mechanistic Studies of Pd-Catalyzed Regioselective Aryl C-H Bond Functionalization with Strained Alkenes: Origin of Regioselectivity [J].
Chai, David I. ;
Thansandote, Praew ;
Lautens, Mark .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (29) :8175-8188