Asymmetric Cross-Coupling of Aryl Triflates to the Benzylic Position of Benzylamines

被引：64

作者：

McGrew, Genette I. ^{[2
]}

Stanciu, Corneliu ^{[2
]}

Zhang, Jiadi ^{[2
]}

Carroll, Patrick J. ^{[2
]}

Dreher, Spencer D. ^{[1
]}

Walsh, Patrick J. ^{[2
]}

机构：

[1] Merck & Co Inc, Dept Proc Res, Rahway, NJ 07065 USA

[2] Univ Penn, Dept Chem, UPenn Merck High Throughput Experimentat Labs, Philadelphia, PA 19104 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 46期

基金：

美国国家科学基金会;

关键词：

asymmetric catalysis; C?C coupling; chromium; palladium; synthetic methods; CARBON-HYDROGEN BONDS; (ETA(6)-ARENE)TRICARBONYLCHROMIUM COMPLEXES; REACTIVITY; ARYLATION; HETEROARYL; GENERATION; CATALYSIS; RADICALS; ALCOHOLS; CATIONS;

D O I：

10.1002/anie.201201874

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Ligand in a haystack: The first catalytic asymmetric cross-coupling of benzyllithiums α to tertiary amines using [Cr(CO)3] activation of benzylic C sp 3-H bonds is described. The stabilized organolithium undergoes Pd-catalyzed coupling with aryl triflates (ArOTf) by a novel dynamic kinetic resolution to yield enantioenriched diarylmethylamines. The chiral ligand for this reaction was identified using high-throughput experimentation with 192 ligands. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：11510 / 11513

页数：4

共 36 条

[1] Metal-catalyzed direct alkylations of (hetero)arenes via C-H bond cleavages with unactivated alkyl halides [J].

Ackermann, Lutz .

CHEMICAL COMMUNICATIONS, 2010, 46 (27) :4866-4877

[2] Palladium- and Copper-Catalyzed Arylation of Carbon-Hydrogen Bonds [J].

Daugulis, Olafs ;

Do, Hien-Quang ;

Shabashov, Dmitry .

ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (08) :1074-1086

[3] Synthesis and reactivity of new cyclomanganated (eta(6)-arene)tricarbonylchromium complexes [J].

Djukic, JP ;

Maisse, A ;

Pfeffer, M ;

deCian, A ;

Fischer, J .

ORGANOMETALLICS, 1997, 16 (04) :657-667

[4] Efficient cross-coupling of secondary alkyltrifluoroborates with aryl chlorides-reaction discovery using parallel microscale experimentation [J].

Dreher, Spencer D. ;

Dormer, Peter G. ;

Sandrock, Deidre L. ;

Molander, Gary A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (29) :9257-+

[5] Structure Formation Principles and Reactivity of Organolithium Compounds [J].

Gessner, Viktoria H. ;

Daeschlein, Christian ;

Strohmann, Carsten .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (14) :3320-3334

[6] CHIRAL BETA-DIMETHYLAMINOALKYLPHOSPHINES - HIGHLY EFFICIENT LIGANDS FOR A NICKEL-COMPLEX CATALYZED ASYMMETRIC GRIGNARD CROSS-COUPLING REACTION [J].

HAYASHI, T ;

FUKUSHIMA, M ;

KONISHI, M ;

KUMADA, M .

TETRAHEDRON LETTERS, 1980, 21 (01) :79-82

[7]

Hevia, 2011, ANGEW CHEM, V123, P6576

[8] Split Personality of Lithium Chloride: Recent Salt Effects in Organometallic Recipes [J].

Hevia, Eva ;

Mulvey, Robert E. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (29) :6448-6450

[9] Advances in Transition Metal (Pd,Ni,Fe)-Catalyzed Cross-Coupling Reactions Using Alkyl-organometallics as Reaction Partners [J].

Jana, Ranjan ;

Pathak, Tejas P. ;

Sigman, Matthew S. .

CHEMICAL REVIEWS, 2011, 111 (03) :1417-1492

[10]

Jaouen G., 1980, J. Organomet. Chem, V195, pC9

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