The developed methodology describes an efficient Rh(III)-catalyzed oxidative C-H/C-H cross-coupling between acyclic enamides and heteroarenes. This cross dehydrogenative coupling (CDC) reaction offers advantages, including excellent regioselectivity and stereoselectivity, good functional group compatibility, and a broad substrate scope. Mechanistically, Rh(III)-catalyzed β-C(sp)-H activation of acyclic enamides is proposed to be the critical step.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.orglett.3c01786 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Amide-Directed Highly Enantioselective Hydrogenation of Diverse Acyclic Multisubstituted Alkenes Under Mild Conditions.
Angew Chem Int Ed Engl
January 2025
Center of Basic Molecular Science (CBMS), Department of Chemistry, Tsinghua University, Beijing, 100084, China.
Enantioselective hydrogenation of tetrasubstituted alkenes to form 1,2-contiguous stereocenters is a particularly appealing but highly challenging transformation in asymmetric catalysis. Despite the notable progress achieved in enantioselective hydrogenation over the past decades, enantioselective hydrogenation of all-carbon tetrasubstituted alkenes containing multiple alkyl groups remains an unsolved challenge. Here, we report a rhodium-catalyzed highly diastereo- and enantioselective hydrogenation of diverse acyclic multisubstituted alkenes under mild conditions.
View Article and Find Full Text PDFRhodium(III)-Catalyzed Switchable β-C(sp)-H Alkenylation and Alkylation of Acyclic Enamides with Allyl Alcohols.
Org Lett
May 2024
Department of Chemistry & Chemical Engineering, Gannan Normal University, Ganzhou 341000, China.
Herein, rhodium(III)-catalyzed β-C(sp)-H alkenylation and alkylation of enamides are presented using readily accessible allylic alcohols by switching the reaction conditions. This tunable transformation has been applied to a wide range of substrates and typically proceeded with excellent regioselectivity and stereoselectivity as well as with good functional group tolerance. The catalytic system offers an efficient approach for synthesizing various functionalized enamides bearing -(2,4)-butadiene and ()-β-C(sp)-H alkylated enamides.
View Article and Find Full Text PDFMetal-Free Stereoconvergent C-H Borylation of Enamides.
Angew Chem Int Ed Engl
October 2023
State Key Laboratory of Coordination Chemistry, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, Jiangsu, 210093, China.
Enamides, functional derivatives of enamines, play a significant role as synthetic targets. However, the stereoselective synthesis of these molecules has posed a longstanding challenge in organic chemistry, particularly for acyclic enamides that are less thermodynamically stable. In this study, we present a general strategy for constructing β-borylenamides by C-H borylation, which provides a versatile platform for generating the stereodefined enamides.
View Article and Find Full Text PDFBrønsted-Acid-Catalyzed In Situ Formation of Acyclic Tertiary Enamides and Its Application to the Preparation of Diverse Nitrogen-Containing Heterocyclic Compounds.
Org Lett
August 2023
Molecular Synthesis Center & Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, 5 Yushan Road, Qingdao 266003, China.
A Brønsted acid-catalyzed cascade process, involving in situ formation of acyclic tertiary enamides and intramolecular Michael reaction, is developed for the synthesis of functionalized cyclic tertiary enamides. Based on the dual reactivities of the enamide moiety, several reaction sequences were realized by using rationally designed substrates, leading to biologically relevant nitrogen-containing heterocyclic compounds with diverse structural skeletons in a concise and diastereocontrolled manner.
View Article and Find Full Text PDFSelective Cross-Dehydrogenative Coupling of Various Acyclic Enamides with Heteroarenes via Rh(III)-Catalyzed C-H Activation.
Org Lett
July 2023
College of Chemistry, Nanchang University, Nanchang, Jiangxi 330031, China.
The developed methodology describes an efficient Rh(III)-catalyzed oxidative C-H/C-H cross-coupling between acyclic enamides and heteroarenes. This cross dehydrogenative coupling (CDC) reaction offers advantages, including excellent regioselectivity and stereoselectivity, good functional group compatibility, and a broad substrate scope. Mechanistically, Rh(III)-catalyzed β-C(sp)-H activation of acyclic enamides is proposed to be the critical step.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!