Transition-Metal-Catalyzed Ketone α-Alkylation and Alkenylation with Simple Alkenes and Alkynes through a Dual Activation Strategy

Hee Nam Lim; Dong Xing; Guangbin Dong

doi:10.1055/s-0037-1610315

Synlett, Inhaltsverzeichnis

Synlett 2019; 30(06): 674-684
DOI: 10.1055/s-0037-1610315

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Transition-Metal-Catalyzed Ketone α-Alkylation and Alkenylation with Simple Alkenes and Alkynes through a Dual Activation Strategy

Hee Nam Lim

^aEco-Friendly New Materials Research Center, Therapeutics and Biotechnology Division, Korea Research Institute of Chemical Technology (KRICT), 141 Gajeong-ro, Yuseong-gu, Daejeon 34114, Republic of Korea

,

Dong Xing

^bShanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200062, P. R. of China

,

Guangbin Dong*

^cDepartment of Chemistry, University of Chicago, Chicago, IL 60637, USA eMail: gbdong@uchicago.edu

› Institutsangaben

Abstract

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Abstract

In this personal account, we summarize our investigations on the α-alkylation and α-alkenylation reactions of ketones with nonactivated alkenes and alkynes, respectively. The serendipitous discovery of C–H alkylation/alkenylation of cyclic 1,2-diketones provided a proof of concept for a dual activation strategy. Extension to the α-alkylation and α-alkenylation of regular ketones was achieved by using 7-azaindoline as a bifunctional ligand. Subsequently, intramolecular coupling between ketones and olefins was achieved with Rh- and Ru-based systems, respectively. Finally, branched-selective α-alkylation was achieved through an Ir-catalyzed enamide-mediated C–H alkylation.

1 Introduction

2 Serendipitous Discovery of α-Alkylation and α-Alkenylation of 1,2-Diketones through Enamine-Mediated C–H Activation

3 Intermolecular Ketone α-Alkylation of Regular Ketones with Nonactivated Olefins

4 Intermolecular Ketone α-Alkenylation of Regular Ketones with Nonactivated Alkynes

5 Intramolecular Ketone α-Alkylation of Regular Ketones with Nonactivated Olefins

6 Branched-Selective α-Alkylation of Regular Ketones with Nonactivated Olefins

7 Conclusions and Outlook

Key words

ketones - alkylation - alkenylation - directing groups - bifunctional catalysis - C-H activation

Volltext

Referenzen

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