Using Rh(III)-Catalyzed C-H Activation as a Tool for the Selective Functionalization of Ketone-Containing Molecules

被引：62

作者：

Boultadakis-Arapinis, Melissa ^{[1
]}

Hopkinson, Matthew N. ^{[1
]}

Glorius, Frank ^{[1
]}

机构：

[1] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 06期

基金：

欧洲研究理事会;

关键词：

CATALYZED ARYLATION; ROBUSTNESS SCREEN; RAPID ASSESSMENT; ALKENYLATION; EFFICIENT; BONDS; ALKENES; ALKYNES; ACCESS; OLEFINATION;

D O I：

10.1021/ol500258q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Due to the strong potential of C H activation in many areas of organic chemistry, the use of a pre-existing carbonyl group for the installation of a directing group to enable selective and predictable alpha-alkenylation with activated olefins as coupling partners is described. This Heck-type reaction would then lead either to beta,gamma-unsaturated ketones or to variously substituted 1,4-butadienes depending on the conditions used for the cleavage of the directing group.

引用

页码：1630 / 1633

页数：4

共 70 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] 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

[3] Palladium- and Nickel-Catalyzed Alkenylation of Enolates [J].

Ankner, Tobias ;

Cosner, Casey C. ;

Helquist, Paul .

CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (06) :1858-1871

[4] N,N-Diethyl O-Carbamate: Directed Metalation Group and Orthogonal Suzuki-Miyaura Cross-Coupling Partner [J].

Antoft-Finch, Aurora ;

Blackburn, Tom ;

Snieckus, Victor .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (49) :17750-17752

[5] Transition metal-catalyzed arylation of unactivated C(sp3)-H bonds [J].

Baudoin, Olivier .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :4902-4911

[6] C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents [J].

Beccalli, Egle M. ;

Broggini, Gianluigi ;

Martinelli, Michela ;

Sottocornola, Silvia .

CHEMICAL REVIEWS, 2007, 107 (11) :5318-5365

[7] Enantioselective Decarboxylative Alkylation Reactions: Catalyst Development, Substrate Scope, and Mechanistic Studies [J].

Behenna, Douglas C. ;

Mohr, Justin T. ;

Sherden, Nathaniel H. ;

Marinescu, Smaranda C. ;

Harned, Andrew M. ;

Tani, Kousuke ;

Seto, Masaki ;

Ma, Sandy ;

Novak, Zoltan ;

Krout, Michael R. ;

McFadden, Ryan M. ;

Roizen, Jennifer L. ;

Enquist, John A., Jr. ;

White, David E. ;

Levine, Samantha R. ;

Petrova, Krastina V. ;

Iwashita, Akihiko ;

Virgil, Scott C. ;

Stoltz, Brian M. .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (50) :14199-14223

[8] Transition Metal-Catalyzed Direct Arylation of Substrates with Activated sp3-Hybridized C-H Bonds and Some of Their Synthetic Equivalents with Aryl Halides and Pseudohalides [J].

Bellina, Fabio ;

Rossi, Renzo .

CHEMICAL REVIEWS, 2010, 110 (02) :1082-1146

[9] RhIII-Catalyzed Oxidative Olefination of Vinylic C-H Bonds: Efficient and Selective Access to Di-unsaturated α-Amino Acid Derivatives and Other Linear 1,3-Butadienes [J].

Besset, Tatiana ;

Kuhl, Nadine ;

Patureau, Frederic W. ;

Glorius, Frank .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (26) :7167-7171

[10] EFFICIENCY OF ORGANOMETALLIC CATALYSIS IN A NEW ECOLOGICAL SYNTHESIS OF RETINAL [J].

BIENAYME, H .

TETRAHEDRON LETTERS, 1994, 35 (40) :7383-7386

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