Efficient syntheses of α-branched amines by three- and four-component C-H functionalization employing a diversifiable hydrazone directing group have been developed. The hydrazone in the α-branched amine products has been readily converted to multiple desirable functionalities such as a nitrile, a carboxylic acid, alkenes, and heterocycles using diverse heterolytic chemistry and homolytic transition metal- or photoredox-catalyzed processes. This study represents the first example of a four-component C-H functionalization reaction.
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http://dx.doi.org/10.1021/acs.orglett.1c03807 | DOI Listing |
Org Lett
March 2024
College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, China.
The difunctionalization of alkenes using aryl thianthrenium salts as the aryl sources has been reported sporadically. However, the four-component difunctionalization of alkenes on the basis of aryl thianthrenium salts has not been reported thus far and still remains a challenge. Herein, a visible light/copper catalysis-enabled four-component reaction of aryl thianthrenium salts, DABCO·(SO), alkenes, and TMSN is presented, which affords a facile approach to β-azidosulfones in good yields with broad substrate scope and excellent functional group tolerance.
View Article and Find Full Text PDFAs an important class of multicomponent reactions, the palladium/norbornene (Pd/NBE) cooperative catalysis has been mainly restricted to the coupling of an aryl halide, an electrophile and a nucleophile. Here, we report the development of a Pd/NBE-catalyzed four-component reaction, which involves C-H amination/ conjunctive coupling using an alkene and an external nucleophile. The use of alkene-tethered nitrogen electrophiles provides a rapid and modular synthesis of 3,3-disubstituted indolines from readily available aryl iodides.
View Article and Find Full Text PDFMolecules
June 2022
Institute of Organic Chemistry, Karlsruhe Institute of Technology, 76131 Karlsruhe, Germany.
In this review, we focus on some interesting and recent examples of various applications of organic azides such as their intermolecular or intramolecular, under thermal, catalyzed, or noncatalyzed reaction conditions. The aforementioned reactions in the aim to prepare basic five-, six-, organometallic heterocyclic-membered systems and/or their fused analogs. This review article also provides a report on the developed methods describing the synthesis of various heterocycles from organic azides, especially those reported in recent papers (till 2020).
View Article and Find Full Text PDFOrg Lett
December 2021
Department of Chemistry, Yale University, New Haven, Connecticut 06520, United States.
Angew Chem Int Ed Engl
December 2021
Institute of Chemistry, The Hebrew University of Jerusalem, Jerusalem, 9190401, Israel.
Organophosphonium salts containing C(sp )- P bonds are among the most utilized reagents in organic synthesis for constructing C-C double bonds. However, their use as C-selective electrophilic groups is rare. Here, we explore an efficient and general transition-metal-free method for sequential chemo- and regioselective C-H and C(sp )- P bond functionalizations.
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