A facile and efficient approach for the synthesis of the CF-containing dioxodibenzothiazepines has been developed via copper-catalyzed trifluoromethylation/cyclization of alkynes utilizing a radical relay strategy. This method has demonstrated low catalyst loading, high regiocontrol, and broad scope under mild conditions. Good compatibility for the N-protecting group, gram-scale experiment, and further derivation of product prove the versatility of this transformation.
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Copper-Catalyzed Trifluoromethylation/Cyclization of Alkynes for Synthesis of Dioxodibenzothiazepines.
Org Lett
March 2021
Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui 230026, China.
A facile and efficient approach for the synthesis of the CF-containing dioxodibenzothiazepines has been developed via copper-catalyzed trifluoromethylation/cyclization of alkynes utilizing a radical relay strategy. This method has demonstrated low catalyst loading, high regiocontrol, and broad scope under mild conditions. Good compatibility for the N-protecting group, gram-scale experiment, and further derivation of product prove the versatility of this transformation.
View Article and Find Full Text PDFSynthesis of Trifluoromethylated Naphthoquinones via Copper-Catalyzed Cascade Trifluoromethylation/Cyclization of 2-(3-Arylpropioloyl)benzaldehydes.
Org Lett
March 2017
Department of Chemistry, Zhejiang Normal University, 688 Yingbin Road, Jinhua 321004, China.
A novel copper-catalyzed cascade trifluoromethylation/cyclization of 2-(3-arylpropioloyl)benzaldehydes is described, allowing a direct access to structurally diverse trifluoromethylated naphthoquinones under mild reaction conditions. It represents the first trans-acyltrifluoromethylation of internal alkynes.
View Article and Find Full Text PDFTfNHNHBoc as a Trifluoromethylating Agent for Vicinal Difunctionalization of Terminal Alkenes.
Org Lett
August 2016
Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, China.
An unprecedented application of trifluoromethanesulfonyl hydrazides as trifluoromethylating agents has been demonstrated in two vicinal difunctionalization reactions of terminal alkenes: the copper-catalyzed three-component vicinal chlorotrifluoromethylation of arylakenes with TfNHNHBoc and NaCl and the tandem trifluoromethylation/cyclization of N-arylacrylamides with TfNHNHBoc. The reactions proceeded in the presence of inexpensive oxidants under mild conditions and provided a range of structurally diverse trifluoromethyl-containing compounds with high regioselectivity.
View Article and Find Full Text PDFCopper-catalyzed trifluoromethylation-cyclization of enynes: highly regioselective construction of trifluoromethylated carbocycles and heterocycles.
Chemistry
October 2013
State key Laboratory of Applied Organic Chemistry lanzhou University, Lanzhou 730000 (P. R. China), Fax: (+86) 931-891-2582.
Regioselective trifluoromethylation-cyclization: A method for copper-catalyzed trifluoromethylation-cyclization of simple enynes using the CC triple bond as a nucleophile is reported for the first time. The reaction proceeds efficiently in a highly regioselective manner to give various 5- or 6-exo-dig carbocycles and heterocycles in moderate to high yields.
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