Coupling between vinyl or aryl iodides and vinyl zinc bromides(either bearing an alkoxy moiety or trisubstituted) under Pd(0) Catalysis

Labaudinière, L.; Normant, Jean F.

doi:10.1016/s0040-4039(00)60026-6

Cited by 21 publications

(5 citation statements)

References 9 publications

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“…A pertinent example that has been expansive in the exploration of 2D chemical space is stereoretentive (sp 2 −sp 2 ) cross-coupling. 223 Simple geometrically defined electrophilic precursors such as alkenyl halides and pseudo-halides, 224 together with nucleophilic alkene components containing, boron, 225 silicon, 226 tin, 227 and zinc, 228 have collectively been leveraged with great success. In general, the predefined geometry of the alkenyl precursor is retained in the product with minimal erosion of stereochemical information (Scheme 21, left).…”

Section: Exploration Of 2d and 3d Chemical Spacementioning

confidence: 99%

Advances in theE → ZIsomerization of Alkenes Using Small Molecule Photocatalysts

et al. 2021

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Geometrical E → Z alkene isomerization is intimately entwined in the historical fabric of organic photochemistry and is enjoying a renaissance (Roth et al. Angew. Chem., Int. Ed. Engl. 1989 28, 1193–1207). This is a consequence of the fundamental stereochemical importance of Z-alkenes, juxtaposed with frustrations in thermal reactivity that are rooted in microscopic reversibility. Accessing excited state reactivity paradigms allow this latter obstacle to be circumnavigated by exploiting subtle differences in the photophysical behavior of the substrate and product chromophores: this provides a molecular basis for directionality. While direct irradiation is operationally simple, photosensitization via selective energy transfer enables augmentation of the alkene repertoire to include substrates that are not directly excited by photons. Through sustained innovation, an impressive portfolio of tailored small molecule catalysts with a range of triplet energies are now widely available to facilitate contra-thermodynamic and thermo-neutral isomerization reactions to generate Z-alkene fragments. This review is intended to serve as a practical guide covering the geometric isomerization of alkenes enabled by energy transfer catalysis from 2000 to 2020, and as a logical sequel to the excellent treatment by Dugave and Demange (Chem. Rev. 2003 103, 2475–2532). The mechanistic foundations underpinning isomerization selectivity are discussed together with induction models and rationales to explain the counterintuitive directionality of these processes in which very small energy differences distinguish substrate from product. Implications for subsequent stereospecific transformations, application in total synthesis, regioselective polyene isomerization, and spatiotemporal control of pre-existing alkene configuration in a broader sense are discussed.

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Section: Exploration Of 2d and 3d Chemical Spacementioning

confidence: 99%

Advances in theE → ZIsomerization of Alkenes Using Small Molecule Photocatalysts

et al. 2021

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“…The reactivity of the second metal is lower than the reactivity of the first due to the vinylic character of the remaining metal and also to the intramolecular chelation by the heteroatom. However, it can be deuterolyzed, iodinolyzed, or coupled with a vinyl iodide under palladium catalysis in the presence of a stoichiometric amount of copper salt in DMA or DMF …”

Section: Synthesis and Reactivity Of Allylic Dimetallic Zinc Reagentsmentioning

confidence: 99%

“…However, it can be deuterolyzed, iodinolyzed, or coupled with a vinyl iodide under palladium catalysis in the presence of a stoichiometric amount of copper salt in DMA or DMF. 156 Metalated allenes can also be prepared by carbolithiation of activated enynes. In this case, the subsequent addition of allylzinc bromide followed by an acidic deuterolysis leads to a 88/12 mixture of geometric isomers 154 (Scheme 113).…”

Section: Synthesis and Reactivity Of Allylic Dimetallic Zinc Reagentsmentioning

confidence: 99%

Synthesis and Reactivity of sp³-Geminated Organodimetallics

1996

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“…A differentiation of the two carbon−metal bonds under cross-coupling reactions with electrophiles provides a versatile method for the formation of two types of carbon−carbon bond in a single operation. Although a number of organodimetallic compounds have been prepared, allylic-type dimetallic compounds such as A remain unexplored and only a few examples such as M = Li, , Zn, − and Sn , have been reported. During the investigation on a series of organoindium reagents, we reported the preparation of diindiopropene A by oxidative addition of indium to 3-bromo-1-iodopropene ( 1a ) .…”

Section: Introductionmentioning

confidence: 99%

Allylic-Type Diindium Reagents. Reactivity toward Electrophiles and Cascade Coupling Reactions with Imines

et al. 2003

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The allylic-type diindium reagents A and B were prepared from 3-bromo-1-iodopropene (1a) and 4-bromo-2-iodobut-2-ene (1b), respectively, and their reactions with electrophiles were investigated. The diindium reagents A and B were initially reacted with imines and the resulting vinylindium compounds were then treated with organic halides in the presence of Pd(PPh(3))(4) to give linear N-aryl and N-tosyl homoallylic amines. Diindium A is stable in a small amount of water in solvent, whereas B is easily protonated to give a crotylindium reagent. The reaction of B with benzaldehyde gives mainly the 1,3- and 1,5-diols via a spontaneous coupling with two molecules of the aldehyde, in contrast to A, which reacts with one molecule of carbonyl compounds to give the vinylindium compounds.

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Coupling between vinyl or aryl iodides and vinyl zinc bromides(either bearing an alkoxy moiety or trisubstituted) under Pd(0) Catalysis

Cited by 21 publications

References 9 publications

Advances in theE → ZIsomerization of Alkenes Using Small Molecule Photocatalysts

Advances in theE → ZIsomerization of Alkenes Using Small Molecule Photocatalysts

Synthesis and Reactivity of sp³-Geminated Organodimetallics

Allylic-Type Diindium Reagents. Reactivity toward Electrophiles and Cascade Coupling Reactions with Imines

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Coupling between vinyl or aryl iodides and vinyl zinc bromides(either bearing an alkoxy moiety or trisubstituted) under Pd(0) Catalysis

Cited by 21 publications

References 9 publications

Advances in theE → ZIsomerization of Alkenes Using Small Molecule Photocatalysts

Advances in theE → ZIsomerization of Alkenes Using Small Molecule Photocatalysts

Synthesis and Reactivity of sp3-Geminated Organodimetallics

Allylic-Type Diindium Reagents. Reactivity toward Electrophiles and Cascade Coupling Reactions with Imines

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Product

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Synthesis and Reactivity of sp³-Geminated Organodimetallics