Manganese(I)-Catalyzed C-H Activation/Diels-Alder/retro-Diels-Alder Domino Alkyne Annulation featuring Transformable Pyridines

被引：63
作者：
Zhu, Cuiju [1 ]
Kuniyil, Rositha [1 ]
Ackermann, Lutz [1 ]
机构：
[1] Georg August Univ Gottingen, Inst Organ & Biomol Chem, Tammannstr 2, D-37077 Gottingen, Germany
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2019年 / 58卷 / 16期
关键词：
C-H activation; domino reactions; indolone alkaloids; manganese; pericyclic reactions; DIRECTING GROUP; CATALYZED SYNTHESIS; FUNCTIONALIZATION; ACCESS; KEY; ALKENYLATION; ARYLATION; ALDEHYDES; ALKENES; ESTERS;
D O I：
10.1002/anie.201900495
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Complexity-increasing Domino reactions comprising C-H allenylation, a Diets-Alder reaction, and a retro-Diels-Alder reaction were realized by a versatile catalyst derived from earth-abundant, non-toxic manganese. The C-H activation/Diels-Alder/retro-Diels-Alder alkyne annulation sequence provided step-economical access to valuable indolone alkaloid derivatives through a facile organometallic C-H activation manifold with transformable pyridines.
引用
收藏
页码：5338 / 5342
页数：5
相关论文
共 106 条
[1]  
Ackermann L., 2009, ANGEW CHEM, V121, P9976, DOI DOI 10.1002/ANGE.200902996
[2]   Domino N-H/C-H bond activation: Palladium-catalyzed synthesis of annulated heterocycles using dichloro(hetero)arenes [J].
Ackermann, Lutz ;
Althammer, Andreas .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (10) :1627-1629
[3]   Robust Ruthenium(II)-Catalyzed C-H Arylations: Carboxylate Assistance for the Efficient Synthesis of Angiotensin-II-Receptor Blockers [J].
Ackermann, Lutz .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2015, 19 (01) :260-269
[4]   Carboxylate-Assisted Ruthenium-Catalyzed Alkyne Annulations by C-H/Het-H Bond Functionalizations [J].
Ackermann, Lutz .
ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (02) :281-295
[5]   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
[6]   Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].
Alberico, Dino ;
Scott, Mark E. ;
Lautens, Mark .
CHEMICAL REVIEWS, 2007, 107 (01) :174-238
[7]  
[Anonymous], 2015, ANGEW CHE
[8]  
[Anonymous], 2017, Angew. Chem
[9]  
[Anonymous], 2015, ANGEW CHEM
[10]  
[Anonymous], 2017, ANGEW CHEM
12345678910