Arene-Free Ruthenium(II/IV)-Catalyzed Bifurcated Arylation for Oxidative C-H/C-H Functionalizations

被引：42
作者：
Rogge, Torben [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 / 44期
关键词：
C-H activation; density functional calculations; oxidative catalysis; reaction mechanisms; ruthenium; CATALYZED DIRECT ARYLATION; BOND ACTIVATION; MECHANISTIC INSIGHT; AROMATIC-COMPOUNDS; BENZOIC-ACIDS; ARYL; WATER; CHLORIDES; HYDROSILYLATION; SELECTIVITY;
D O I：
10.1002/anie.201909457
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Experimental and computational studies provide detailed insight into the selectivity- and reactivity-controlling factors in bifurcated ruthenium-catalyzed direct C-H arylations and dehydrogenative C-H/C-H functionalizations. Thorough investigations revealed the importance of arene-ligand-free complexes for the formation of biscyclometalated intermediates within a ruthenium(II/IV/II) mechanistic manifold.
引用
收藏
页码：15640 / 15645
页数：6
相关论文
共 88 条
[1]   Catalytic arylation reactions by C-H bond activation with aryl tosylates [J].
Ackermann, L ;
Althammer, A ;
Born, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (16) :2619-2622
[2]   Phosphine oxides as preligands in ruthenium-catalyzed arylations via C-H bond functionalization using aryl chlorides [J].
Ackermann, L .
ORGANIC LETTERS, 2005, 7 (14) :3123-3125
[3]  
Ackermann L., 2007, ANGEW CHEM, V119, P6482
[4]  
Ackermann L., 2009, ANGEW CHEM, V121, P9976, DOI DOI 10.1002/ANGE.200902996
[5]   [RuCl3(H2O)n]-catalyzed direct arylations [J].
Ackermann, Lutz ;
Althammer, Andreas ;
Born, Robert .
TETRAHEDRON, 2008, 64 (26) :6115-6124
[6]   [RuCl3(H2O)n]-catalyzed direct arylations with bromides as electrophiles [J].
Ackermann, Lutz ;
Althammer, Andreas ;
Born, Robert .
SYNLETT, 2007, (18) :2833-2836
[7]   Ruthenium(IV) alkylidenes as precatalysts for direct arylations of Alkenes with aryl chlorides and an application to sequential catalysis [J].
Ackermann, Lutz ;
Born, Robert ;
Alvarez-Bercedo, Paula .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (33) :6364-6367
[8]   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
[9]   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
[10]   Ruthenium-Catalyzed Direct C-H Bond Arylations of Heteroarenes [J].
Ackermann, Lutz ;
Lygin, Alexander V. .
ORGANIC LETTERS, 2011, 13 (13) :3332-3335
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