Sustainable Manganese-Catalyzed Solvent-Free Synthesis of Pyrroles from 1,4-Diols and Primary Amines

被引：66
作者：
Borghs, Jannik C. [1 ]
Lebedev, Yury [2 ]
Rueping, Magnus [1 ,2 ]
El-Sepelgy, Osama [1 ]
机构：
[1] Rhein Westfal TH Aachen, Inst Organ Chem, Landoltweg 1, D-52074 Aachen, Germany
[2] KAUST, KCC, Thuwal 239556900, Saudi Arabia
来源：
ORGANIC LETTERS | 2019年 / 21卷 / 01期
关键词：
BORROWING HYDROGEN; N-HETEROCYCLIZATION; ALPHA-ALKYLATION; MULTICOMPONENT SYNTHESIS; SECONDARY ALCOHOLS; COOPERATIVE METAL; IRON CATALYSIS; CYCLIC IMIDES; RUTHENIUM; KETONES;
D O I：
10.1021/acs.orglett.8b03506
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A general and selective metal-catalyzed conversion of biomass-derived primary diols and amines to the highly valuable 2,5-unsubstituted pyrroles has been developed. The reaction is catalyzed by a stable nonprecious manganese complex (1 mol %) in the absence of organic solvents whereby water and molecular hydrogen are the only side products. The manganese catalyst shows unprecedented selectivity, avoiding the formation of pyrrolidines, cyclic imides, and lactones.
引用
收藏
页码：70 / 74
页数：5
相关论文
共 90 条
[1]  
[Anonymous], CHEMSUSCHEM
[2]   Iron Catalysis in Organic Synthesis [J].
Bauer, Ingmar ;
Knoelker, Hans-Joachim .
CHEMICAL REVIEWS, 2015, 115 (09) :3170-3387
[3]   Transfer Hydrogenation of Carbonyl Derivatives Catalyzed by an Inexpensive Phosphine-Free Manganese Precatalyst [J].
Bruneau-Voisine, Antoine ;
Wang, Ding ;
Dorcet, Vincent ;
Roisnel, Thierry ;
Darcel, Christophe ;
Sortais, Jean-Baptiste .
ORGANIC LETTERS, 2017, 19 (13) :3656-3659
[4]   Mono-N-methylation of anilines with methanol catalyzed by a manganese pincer-complex [J].
Bruneau-Voisine, Antoine ;
Wang, Ding ;
Dorcet, Vincent ;
Roisnel, Thierry ;
Darcel, Christophe ;
Sortais, Jean-Baptiste .
JOURNAL OF CATALYSIS, 2017, 347 :57-62
[5]   Highly Chemo- and Stereoselective Transfer Semihydrogenation of Alkynes Catalyzed by a Stable, Well-Defined Manganese(II) Complex [J].
Brzozowska, Aleksandra ;
Azofra, Luis Miguel ;
Zubar, Viktoriia ;
Atodiresei, Iuliana ;
Cavallo, Luigi ;
Rueping, Magnus ;
El-Sepelgy, Osama .
ACS CATALYSIS, 2018, 8 (05) :4103-4109
[6]  
Bullock R. M., 2010, Catalysis without Precious Metals, V1
[7]   Ruthenium and osmium complexes in C-C bond-forming reactions by borrowing hydrogen catalysis [J].
Chelucci, Giorgio .
COORDINATION CHEMISTRY REVIEWS, 2017, 331 :1-36
[8]   Getting Down to Earth: The Renaissance of Catalysis with Abundant Metals [J].
Chink, Paul ;
Morris, Robert .
ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (09) :2495-2495
[9]   PREPARATION OF CIS AND TRANS 2,5-DIMETHOXY-2-(ACETAMIDOMETHYL)-2,5-DIHYDROFURAN, OF CISS AND TRANS 2,5-DIMETHOXY-2-(ACETAMIDOMETHYL)-TETRAHYDROFURAN AND OF 1-PHENYL-2-(ACETAMIDOMETHYL)-PYRROLE [J].
CLAUSONKAAS, N ;
TYLE, Z .
ACTA CHEMICA SCANDINAVICA, 1952, 6 (05) :667-670
[10]   Advances in One-Pot Synthesis through Borrowing Hydrogen Catalysis [J].
Corma, Avelino ;
Navas, Javier ;
Sabater, Maria J. .
CHEMICAL REVIEWS, 2018, 118 (04) :1410-1459
123456789