Esters are important chemicals widely used in various areas, and alkoxycarbonylation represents one of the most powerful tools for their synthesis. In this communication, a new copper-catalyzed carbonylative procedure for the synthesis of aliphatic esters from cycloalkanes and alcohols was developed. Through direct activation of the Csp3 -H bond of alkanes and with alcohols as the nucleophiles, the desired esters were prepared in moderate-to-good yields. Paraformaldehyde could also be applied for in situ alcohol generation by radical trapping, and moderate yields of the corresponding esters could be produced. Notably, this is the first report on copper-catalyzed alkoxycarbonylation of alkanes.
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http://dx.doi.org/10.1002/cssc.201601587 | DOI Listing |
Org Lett
October 2021
Leibniz-Institut für Katalyse e.V., Albert-Einstein-Straße 29a, 18059 Rostock, Germany.
A copper-catalyzed alkoxycarbonylation transformation of unactivated alkyl iodides has been developed. Various alkyl iodides can be converted into the corresponding -butyl esters in good yields. NaOBu acts as both a nucleophile and a base.
View Article and Find Full Text PDFJ Org Chem
July 2021
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering, Soochow University, 199 Renai Street, Suzhou, Jiangsu 215123, China.
A new approach for the preparation of carbamates the copper-catalyzed cross-coupling reaction of amines with alkoxycarbonyl radicals generated from carbazates is described. This environmentally friendly protocol takes place under mild conditions and is compatible with a wide range of amines, including aromatic/aliphatic and primary/secondary substrates.
View Article and Find Full Text PDFOrg Lett
June 2019
School of Materials Science and Engineering, Center for Supramolecular Chemistry and Catalysis and Department of Chemistry , Shanghai University, 99 Shang-Da Road , Shanghai 200444 , China.
This work emphasizes the synthesis of alkyl esters via Cu-catalyzed and In-mediated alkoxycarbonylation of unactivated alkyl iodides in the presence of In or InI. The reactions were suitable for the preparation of primary, secondary, and even tertiary alkyl esters, representing an exceptionally rare example for the creation of quaternary carbon centers upon formation of esters. The preliminary mechanistic studies indicated that alkyl radicals were involved, and Cu/In/CO played a cooperative role in the carbonylation event.
View Article and Find Full Text PDFChem Sci
July 2018
State Key Laboratory for Oxo Synthesis and Selective Oxidation , Centre for Excellence in Molecular Synthesis , Suzhou Research Institute , Lanzhou Institute of Chemical Physics , University of Chinese Academy of Sciences, Chinese Academy of Sciences , Lanzhou 730000 , China . Email:
A copper(i)-catalyzed dearomative borylation of -alkoxycarbonyl protected indole-3-carboxylates has been developed. The boron addition in this reaction occurred regioselectively at the 2-position of indoles followed by diastereoselective protonation, affording the corresponding stable cyclic chiral α-amino boronates (2-borylindolines) in moderate to good yields with excellent diastereo- and enantioselectivities. The product could be used as a versatile precursor to undergo subsequent stereoselective transformations, delivering highly functionalized 2,3,3-trisubstituted chiral indolines.
View Article and Find Full Text PDFChemSusChem
April 2017
Leibniz-Institut für Katalyse e.V. an der, Universität Rostock, Albert-Einstein-Straße 29a, 18059, Rostock, Germany.
Esters are important chemicals widely used in various areas, and alkoxycarbonylation represents one of the most powerful tools for their synthesis. In this communication, a new copper-catalyzed carbonylative procedure for the synthesis of aliphatic esters from cycloalkanes and alcohols was developed. Through direct activation of the Csp3 -H bond of alkanes and with alcohols as the nucleophiles, the desired esters were prepared in moderate-to-good yields.
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