Light-Driven Single-Electron Transfer Processes as an Enabling Principle in Sulfur and Selenium Multicatalysis

被引:42
作者
Breder, Alexander [1 ,2 ]
Depken, Christian [2 ]
机构
[1] Univ Regensburg, Inst Organ Chem, Univ Str 31, D-93053 Regenburg, Germany
[2] Univ Gottingen, Inst Organ & Biomol Chem, Tammannstr 2, D-37077 Gottingen, Germany
关键词
hydrogen atom transfer; photoredox catalysis; selenium-pi-acids; single-electron transfer; thiyl radicals; BOND-DISSOCIATION ENERGIES; C-H BONDS; ANTI-MARKOVNIKOV HYDROAMINATION; HYDROGEN-ATOM ABSTRACTION; RADICAL-CHAIN HYDROSILYLATION; CARBENE-BORYL RADICALS; COOPERATIVE CATALYSIS; PHOTOREDOX CATALYSIS; SITE-SELECTIVITY; ANODIC-OXIDATION;
D O I
10.1002/anie.201812486
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Cooperativity has become a mainstay in the context of multicatalytic reaction design. The combination of two or more catalysts that possess mechanistically distinct activation principles within a single chemical setting can enable bond constructions that would be impossible for any of the catalysts alone. An emerging subdomain within the field of multicatalysis is characterized by single-electron transfer processes that are sustained by the synergistic merger of sulfur or selenium organocatalysis with photoredox catalysis. From a synthetic viewpoint, such processes have tremendous value, as they can offer new and economic pathways for the concise assembly of complex molecular architectures. Thus, the aim of this Review is to highlight recent methodological progress made in this area and to contextualize representative transformations with the mechanistic underpinnings that enable these reactions.
引用
收藏
页码:17130 / 17147
页数:18
相关论文
共 208 条
[1]   Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].
Ackermann, Lutz .
CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345
[2]   Combinations of Aminocatalysts and Metal Catalysts: A Powerful Cooperative Approach in Selective Organic Synthesis [J].
Afewerki, Samson ;
Cordova, Armando .
CHEMICAL REVIEWS, 2016, 116 (22) :13512-13570
[3]   Synergistic catalysis: A powerful synthetic strategy for new reaction development [J].
Allen, Anna E. ;
MacMillan, David W. C. .
CHEMICAL SCIENCE, 2012, 3 (03) :633-658
[4]   THIOLS AS POLARITY REVERSAL CATALYSTS FOR HYDROGEN-ATOM TRANSFER FROM ORGANOSILANES TO ALKYL RADICALS - REDUCTION OF ALKYL-HALIDES BY TRIETHYLSILANE [J].
ALLEN, RP ;
ROBERTS, BP ;
WILLIS, CR .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (18) :1387-1388
[5]   Multicatalysis: Advancing Synthetic Efficiency and Inspiring Discovery [J].
Ambrosini, Lisa M. ;
Lambert, Tristan H. .
CHEMCATCHEM, 2010, 2 (11) :1373-1380
[6]  
[Anonymous], 2012, ANGEW CHEM, DOI DOI 10.1002/ANIE.201201666
[7]  
[Anonymous], 2017, ANGEW CHEM, V129, P7000
[8]  
[Anonymous], 1982, ANGEW CHEM INT ED EN
[9]  
[Anonymous], ANGEW CHEM
[10]  
Armstrong D.A., 1999, S-Centered Radicals