A novel Lewis base-promoted rearrangement of allylic cyanohydrins has been developed, in which the cyano group was rearranged, directly coupled with the generation of new functional groups. This protocol provides a unique and facile way to prepare highly functionalized nitriles bearing 1,3-diketone moieties under mild reaction conditions. Furthermore, the synthetic transformations of the functionalized products have also been demonstrated.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/jo501909w | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Aluminium porphyrins catalyse the hydrogenation of CO with H.
Chem Sci
December 2024
Department of Inorganic Chemistry, Faculty of Science, Charles University Albertov 6, 128 00 Praha 2 Czech Republic
Boron-based frustrated Lewis pairs (FLPs) have become well-established catalysts for the hydrogenation of a wide range of functional groups. Conversely, aluminium-based FLP hydrogenation catalysts are less common, especially for CO reduction. They are mostly confined to the hydrogenation of imines, alkenes, and alkynes even though aluminium is much more abundant than boron and forms structurally related compounds.
View Article and Find Full Text PDFWeak Base-Promoted Direct Cross-Coupling of Naphthalene-1,8-diaminato-substituted Arylboron Compounds.
JACS Au
October 2024
Graduate School of Advanced Science and Engineering, Hiroshima University, Higashi-Hiroshima 739-8526, Japan.
The indispensability of a base in Suzuki-Miyaura coupling (SMC) employing organoboronic acids/esters is well recognized, which occasionally induces competitive protodeborylation in organoboron reagents. This phenomenon is particularly pronounced in fluorine-substituted aryl and heteroaryl boron compounds. Here, we show that direct SMC of naphthalene-1,8-diaminato (dan)-substituted aryl boron compounds, Ar-B(dan), characterized by its remarkable stability toward protodeborylation due to their diminished boron-Lewis acidity, occurs utilizing a weak base in conjunction with a palladium/copper cooperative catalyst system.
View Article and Find Full Text PDFLewis base promoted [4 + 2] annulation of -acylamino-aryl MBH carbonates with isatin.
Org Biomol Chem
October 2024
Department of Chemistry and Chemical Engineering, Zunyi Normal College, Zunyi 563002, China.
The first example of Lewis base promoted [4 + 2] annulation between -acylamino-aryl MBH carbonates and isatin has been developed. This methodology exhibits excellent substrate applicability and has synthesized 1,4-dihydrospiro benzo[][1,3]oxazine-oxindoles with yields up to 98%. The practical value of this method is underscored by its successful application in a 50-fold scale-up.
View Article and Find Full Text PDFVisible Light-Induced Oxy-perfluoroalkylation of Olefins via Ternary Electron Donor-Acceptor Complexes.
J Org Chem
August 2024
Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Key Laboratory of Research and Development of Natural Products, School of Pharmacy, Yunnan University, Kunming 650500, China.
Perfluoroalkyl iodides generally formed electron donor-acceptor (EDA) complexes by halogen bonding with a nitrogen atom containing Lewis bases. Since the electronegativity of the oxygen atom is stronger than that of the nitrogen atom, the resulting Rf-I···O-type halogen bonding EDA complex is less inclined to undergo electron transfer. Here, we reported rare ternary EDA complexes among perfluoroalkyl iodide, oxygen atom, and base.
View Article and Find Full Text PDFAlicyclic-Amine-Derived Imine-BF Complexes: Easy-to-Make Building Blocks for the Synthesis of Valuable α-Functionalized Azacycles.
Angew Chem Int Ed Engl
January 2024
Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611, USA.
A new strategy to access α-functionalized alicyclic amines via their corresponding imine-BF complexes is reported. Isolable imine-BF complexes, readily prepared via dehydrohalogenation of N-bromoamines in a base-promoted/18-crown-6 catalyzed process followed by addition of boron trifluoride etherate, undergo reactions with a wide range of organometallic nucleophiles to afford α-functionalized azacycles. Organozinc and organomagnesium nucleophiles add at ambient temperatures, obviating the need for cryogenic conditions.
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!