Regioselective syntheses of fully-substituted 1,2,3-triazoles: the CuAAC/C-H bond functionalization nexus

被引：221
作者：
Ackermann, Lutz [1 ]
Potukuchi, Harish Kumar [1 ]
机构：
[1] Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2010年 / 8卷 / 20期
关键词：
PALLADIUM-CATALYZED ARYLATION; AZIDE-ALKYNE CYCLOADDITION; MEDIATED DIRECT ARYLATION; CROSS-COUPLING REACTIONS; C-H; CARBON-HYDROGEN; CLICK CHEMISTRY; ARYL CHLORIDES; 1,3-DIPOLAR CYCLOADDITIONS; DIRECT ALKYNYLATION;
D O I：
10.1039/c0ob00212g
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Regioselective syntheses of 1,4,5-trisubstituted 1,2,3- triazoles were accomplished by three different strategies, relying on (i) the interception of stoichiometrically formed 5-cuprated-1,2,3-triazoles, (ii) the use of stoichiometrically functionalized alkynes or (iii) catalytic C-H bond functionalizations. This perspective article summarizes progress in this research area until June 2010.
引用
收藏
页码：4503 / 4513
页数：11
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[11]   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
[12]   Palladium-Catalyzed Dehydrogenative Direct Arylations of 1,2,3-Triazoles [J].
Ackermann, Lutz ;
Jeyachandran, Rajkumar ;
Potukuchi, Harish K. ;
Novak, Petr ;
Buettner, Lea .
ORGANIC LETTERS, 2010, 12 (09) :2056-2059
[13]   Palladium-Catalyzed Direct Arylations, Alkenylations, and Benzylations through C-H Bond Cleavages with Sulfamates or Phosphates as Electrophiles [J].
Ackermann, Lutz ;
Barfuesser, Sebastian ;
Pospech, Jola .
ORGANIC LETTERS, 2010, 12 (04) :724-726
[14]   Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].
Ackermann, Lutz ;
Vicente, Ruben ;
Kapdi, Anant R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9792-9826
[15]   Regioselective Ruthenium-Catalyzed Direct Benzylations of Arenes through C-H Bond Cleavages [J].
Ackermann, Lutz ;
Novak, Petr .
ORGANIC LETTERS, 2009, 11 (21) :4966-4969
[16]   Catalytic Direct Arylations in Polyethylene Glycol (PEG): Recyclable Palladium(0) Catalyst for C-H Bond Cleavages in the Presence of Air [J].
Ackermann, Lutz ;
Vicente, Ruben .
ORGANIC LETTERS, 2009, 11 (21) :4922-4925
[17]   Ruthenium-Catalyzed Direct Arylations of N-Aryl 1,2,3-Triazoles with Aryl Chlorides as Electrophiles [J].
Ackermann, Lutz ;
Born, Robert ;
Vicente, Ruben .
CHEMSUSCHEM, 2009, 2 (06) :546-549
[18]   Ruthenium-Catalyzed Regioselective Direct Alkylation of Arenes with Unactivated Alkyl Halides through C-H Bond Cleavage [J].
Ackermann, Lutz ;
Novak, Petr ;
Vicente, Ruben ;
Hofmann, Nora .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (33) :6045-6048
[19]   Palladium-Catalyzed Direct Arylations of Heteroarenes with Tosylates and Mesylates [J].
Ackermann, Lutz ;
Althammer, Andreas ;
Fenner, Sabine .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (01) :201-204
[20]   Enhanced reactivity of dinuclear Copper(I) acetylides in dipolar cycloadditions [J].
Ahlquist, Marten ;
Fokin, Valery V. .
ORGANOMETALLICS, 2007, 26 (18) :4389-4391
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