Manganese-Catalyzed α-Alkylation of Ketones, Esters, and Amides Using Alcohols

被引：187
作者：
Chakraborty, Subrata [1 ]
Daw, Prosenjit [1 ]
Ben David, Yehoshoa [1 ]
Milstein, David [1 ]
机构：
[1] Weizmann Inst Sci, Dept Organ Chem, IL-76100 Rehovot, Israel
来源：
ACS CATALYSIS | 2018年 / 8卷 / 11期
基金：
欧洲研究理事会; 以色列科学基金会;
关键词：
alkylation; ketones; secondary alcohol; amides; esters; manganese; pincer; STEREOSELECTIVE TRANSFER SEMIHYDROGENATION; PNP PINCER COMPLEXES; HYDROGENATION CATALYSTS; SUSTAINABLE SYNTHESIS; UNACTIVATED AMIDES; TRIDENTATE LIGAND; BETA-ALKYLATION; N-METHYLATION; IRON; AMINES;
D O I：
10.1021/acscatal.8b03720
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
Herein we report the manganese-catalyzed C-C bond-forming reactions via a-alkylation of ketones, amides, and esters, using primary alcohols. beta-Alkylation of secondary alcohols by primary alcohols to obtain a-alkylated ketones is also reported. The reactions are catalyzed by a (Pr-i-PNP)Mn(H)(CO)(2) pincer complex under mild conditions in the presence of (catalytic) base liberating water (and H-2 in the case of secondary alcohol alkylation) as the sole byproduct.
引用
收藏
页码：10300 / 10305
页数：11
相关论文
共 80 条
[1]   A Stable Manganese Pincer Catalyst for the Selective Dehydrogenation of Methanol [J].
Anderez-Fernandez, Maria ;
Vogt, Lydia K. ;
Fischer, Steffen ;
Zhou, Wei ;
Jiao, Haijun ;
Garbe, Marcel ;
Elangovan, Saravanakumar ;
Junge, Kathrin ;
Junge, Henrik ;
Ludwig, Ralf ;
Beller, Matthias .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (02) :559-562
[2]   Phosphine-Free NNN-Manganese Complex Catalyzed α-Alkylation of Ketones with Primary Alcohols and Friedlander Quinoline Synthesis [J].
Barman, Milan K. ;
Jana, Akash ;
Maji, Biplab .
ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (17) :3233-3238
[3]   Iron Catalysis in Organic Synthesis [J].
Bauer, Ingmar ;
Knoelker, Hans-Joachim .
CHEMICAL REVIEWS, 2015, 115 (09) :3170-3387
[4]   Manganese-Catalyzed Direct Deoxygenation of Primary Alcohols [J].
Bauer, Jonathan O. ;
Chakraborty, Subrata ;
Milstein, David .
ACS CATALYSIS, 2017, 7 (07) :4462-4466
[5]   Modularly designed transition metal PNP and PCP pincer complexes based on aminophosphines: Synthesis and catalytic applications [J].
Benito-Garagorri, David ;
Kirchner, Karl .
ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (02) :201-213
[6]   Carbon dioxide hydrogenation catalysed by well-defined Mn(I) PNP pincer hydride complexes [J].
Bertini, Federica ;
Glatz, Mathias ;
Gorgas, Nikolaus ;
Stoeger, Berthold ;
Peruzzini, Maurizio ;
Veiros, Luis F. ;
Kirchner, Karl ;
Gonsalvi, Luca .
CHEMICAL SCIENCE, 2017, 8 (07) :5024-5029
[7]   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
[8]   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
[9]   Hydrogenation of ketones with a manganese PN3P pincer pre-catalyst [J].
Bruneau-Voisine, Antoine ;
Wang, Ding ;
Roisnel, Thierry ;
Darcel, Christophe ;
Sortais, Jean-Baptiste .
CATALYSIS COMMUNICATIONS, 2017, 92 :1-4
[10]   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
12345678