Carbometallation Reactions

Marek, Ilan; and, Nicka Chinkov; Banon-Tenne, Daniella

doi:10.1002/9783527619535.ch7

Cited by 52 publications

(10 citation statements)

References 215 publications

(248 reference statements)

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“…The carbometalation reaction, − as opposed to all reactions described above, consists in the addition of an organometallic species across the double bond to provide a new organometallic species that can be subjected to subsequent synthetic transformations. 1,2-Bisalkylated derivatives are thus obtained.…”

Section: Direct Functionalization Of Achiral Three-membered Carbocycl...mentioning

confidence: 99%

Asymmetric Preparation of Polysubstituted Cyclopropanes Based on Direct Functionalization of Achiral Three-Membered Carbocycles

2018

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In addition to the appealing synthetic transformations that cyclopropanes present, they are also part of larger molecular structures that possess a wide range of biological properties. Therefore, the preparation of enantiomerically enriched cyclopropanes has consistently been a very interesting research topic in organic synthesis. In this Focus Review, we are presenting new methods for the synthesis of these target compounds through catalytic and asymmetric direct functionalization of simple achiral three-membered carbocycle precursors. These convergent and very flexible approaches allow the preparation of a large variety of polysubstituted alkyl-, vinyl-, alkynyl-, and arylcyclopropanes but also cyclopropanols and cyclopropylamines in very high diastereo- and enantiomeric ratios from a single precursor, underlining the power of this synthetic route.

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Section: Direct Functionalization Of Achiral Three-membered Carbocycl...mentioning

confidence: 99%

Asymmetric Preparation of Polysubstituted Cyclopropanes Based on Direct Functionalization of Achiral Three-Membered Carbocycles

2018

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“…Polycyclic oxygen or nitrogen heterocycles are found in numerous natural products or valuable building blocks, as illustrated in Figure . Because they give an effective access to carbon–carbon bonds, carbometallation reactions can be regarded as a perfect showcase. The transition-metal-catalyzed functionalization of alkynes, which seems to be an easy-to-adapt transformation, is an attractive, possibly stereoselective transformation that provides substituted alkenes.…”

Section: Introductionmentioning

confidence: 99%

Nickel-Catalyzed Electrochemical Cyclization of Alkynyl Aryl Iodide and the Domino Reaction with Aldehydes

et al. 2021

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An intramolecular carbometallation of a triple bond promoted by electrochemistry and mediated by nickel catalysis is described. This domino process transforms various aryl halides bearing a propargyl chain into substituted heterocycles in one single operation, with high stereoselectivities and in good to high yields. This reaction, characterized by a cyclic voltammetry set of experiments, proceeds following a syn-exo-dig cyclization process. When run at 80 °C, vinylbenzofuranes that are suitable substrates for cycloaddition reactions are obtained. Article pubs.acs.org/joc

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“…Similarly, enamides are another important class of substrates involved in numerous applications in organic synthesis [5,15]. As one of the most straightforward and well-developed methods to generate polysubstituted alkenes is the carbometallation reaction of alkynes [16–18], ynamide should be a suitable substrate for the regio- and stereoselective synthesis of enamide through carbometallation reaction [19–22]. Although the stereoselectivity of the carbocupration is usually controlled through a syn -addition of the organocopper reagent on the triple bond [23], the regioselectivity is dependent on the nature of the α-substituent on the alkyne 1 .…”

Section: Introductionmentioning

confidence: 99%

Regio- and stereoselective carbometallation reactions of N-alkynylamides and sulfonamides

Minko¹,

Pasco²,

Chechik³

et al. 2013

Beilstein J. Org. Chem.

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SummaryThe carbocupration reactions of heterosubstituted alkynes allow the regio- and stereoselective formation of vinyl organometallic species. N-Alkynylamides (ynamides) are particularly useful substrates for the highly regioselective carbocupration reaction, as they lead to the stereodefined formation of vinylcopper species geminated to the amide moiety. The latter species are involved in numerous synthetically useful transformations leading to valuable building blocks in organic synthesis. Here we describe in full the results of our studies related to the carbometallation reactions of N-alkynylamides.

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Carbometallation Reactions

Cited by 52 publications

References 215 publications

Asymmetric Preparation of Polysubstituted Cyclopropanes Based on Direct Functionalization of Achiral Three-Membered Carbocycles

Asymmetric Preparation of Polysubstituted Cyclopropanes Based on Direct Functionalization of Achiral Three-Membered Carbocycles

Nickel-Catalyzed Electrochemical Cyclization of Alkynyl Aryl Iodide and the Domino Reaction with Aldehydes

Regio- and stereoselective carbometallation reactions of N-alkynylamides and sulfonamides

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