A removable acyl group promoted the intramolecular didehydro-Diels-Alder reaction of styrene-ynes under mild reaction conditions is proposed. The reaction is free of metals and catalysts, is easy to perform, and exhibits good functional group tolerance, providing a highly chemoselective approach for obtaining the valuable aryldihydronaphthalene derivatives.
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http://dx.doi.org/10.1021/acs.joc.2c00180 | DOI Listing |
Chem Commun (Camb)
September 2023
Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati-781039, India.
A weak acyl chelation-assisted distal C4-H allylation of indoles has been accomplished using vinylcyclopropanes as an allylating agent under redox-neutral ruthenium(II) catalysis. The regioselectivity, removable directing group, substrate scope and diastereoselectivity are the important practical features.
View Article and Find Full Text PDFOrg Lett
January 2023
Department of Chemistry, University of Minnesota-Twin Cities, 207 Pleasant Street SE, Minneapolis, Minnesota 55455, United States.
Directing groups are a common strategy to target traditionally inert bonds, with an easily removable directing group being ideal. Herein we disclose our method for rhodium-catalyzed C-O bond functionalization of -pyridylimidates using a recyclable and traceless amine directing group. In addition to the substrate scope, we discuss the behavior of this class of compounds and how that behavior affects their reactivity.
View Article and Find Full Text PDFJ Org Chem
May 2022
Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China.
A removable acyl group promoted the intramolecular didehydro-Diels-Alder reaction of styrene-ynes under mild reaction conditions is proposed. The reaction is free of metals and catalysts, is easy to perform, and exhibits good functional group tolerance, providing a highly chemoselective approach for obtaining the valuable aryldihydronaphthalene derivatives.
View Article and Find Full Text PDFChemistry
February 2021
State Key Laboratory of Coordination Chemistry, Jiangsu Key, Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210023, P. R. China.
The convenient cross-coupling of sp or sp carbons with a specific boron vertex on carborane cage represents significant synthetic values and insurmountable challenges. In this work, we report an Rh-catalyzed reaction between o-carborane and N-acyl-glutarimides to construct various B -C bonds. Under the optimized condition, the removable imine directing group (DG) leads to B(3)- or B(3,6)-C couplings, while the pyridyl DG leads to B(3,5)-Ar coupling.
View Article and Find Full Text PDFChem Sci
June 2019
College of Chemistry and Chemical Engineering and Key Laboratory of Auxiliary Chemistry and Technology for Chemical Industry , Ministry of Education , Shaanxi University of Science and Technology, Xi'an 710021 , China.
Aryl carboxylic acids are among the most abundant substrates in chemical synthesis and represent a perfect example of a traceless directing group that is central to many processes in the preparation of pharmaceuticals, natural products and polymers. Herein, we describe a highly selective method for the direct step-down reduction of carboxylic acids to arenes, proceeding well-defined Pd(0)/(ii) catalytic cycle. The method shows a remarkably broad substrate scope, enabling to direct the classical acyl reduction towards selective decarbonylation by a redox-neutral mechanism.
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