Stereospecific Synthesis of Temarotene, Its Structural Isomers, and Mixed Triaryl Alkenes from gem-Borazirconocene Alkenes

Deloux, Laurent; Srebnik, Morris; Sabat, Michal

doi:10.1021/jo00116a006

Cited by 37 publications

(20 citation statements)

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“…The coupling of 4-fluorophenyl alkenylborane Z-3bB, and bromobenzene and that of 9 and 1-bromo-4-fluorobenzene produced the isomeric diarylalkenyl products 8 and 10 as a single isomer, respectively. In addition, the Suzuki-Miyaura coupling of 9 and 6-bromo-2,2,3,3-tetrahydro-1,1,4,4-tetramethylnaphthalene (11) produced temarotene 16 (12) without a loss of geometrical purity.…”

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confidence: 99%

Highly regio- and stereoselective synthesis of alkenylboronic esters by copper-catalyzed boron additions to disubstituted alkynes

2011

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mentioning

confidence: 99%

Highly regio- and stereoselective synthesis of alkenylboronic esters by copper-catalyzed boron additions to disubstituted alkynes

2011

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“…Examples of the preparation of E ‐phenylalkenyl boron compounds such as ( E )‐ 3 are limited, and such compounds can be useful for synthesis of 1,2‐bisaryl alkenes having a Z configuration. As an illustration, we targeted two retinoid mimics having a Z configuration.…”

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confidence: 99%

“…The Z ‐configured retinoid derivative 33 was synthesized by a one‐pot procedure involving treatment of ( E )‐ 3 with N ‐chlorosuccinimide (NCS) in 1,4‐dioxane (Scheme ). Water was then added (to form a boronic acid) along with 6‐bromo‐1,1,4,4‐tetramethyl‐1,2,3,4‐tetrahydronaphthalene, PdCl 2 (dppf), and Na 2 CO 3 .…”

Section: Figurementioning

confidence: 99%

Radical trans‐Hydroboration of Alkynes with N‐Heterocyclic Carbene Boranes

et al. 2018

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Hydroboration of internal alkynes with N-heterocyclic carbene boranes (NHC-boranes) occurs to provide stable NHC (E)-alkenylboranes upon thermolysis in the presence of di-tert-butyl peroxide.T he Eisomer results from an unusual trans-hydroboration, and the E/Z selectivity is typically high (90:10 or greater). Evidence suggests that this hydroboration occurs by ar adical-chain reaction involving addition of an NHC-boryl radical to an alkyne to give a b-NHC-borylalkenyl radical. Ensuing hydrogen abstraction from the starting NHC-borane provides the product and returns the starting NHC-boryl radical. Experiments suggest that the observed trans-selectivity results from kinetic control in the hydrogen-transfer reaction. Figure 1. Methods for trans-hydroboration of alkynes.

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“…The regiochemistry of the hydrozirconation of disubstituted stannyl- [24,[167][168][169][170] and silyl- [171] acetylenes and boron- [118,[172][173][174][175] and zinc- [34,126] alkynyl derivatives result in the formation of 1,1-dimetallo compounds. Hydrozirconation of alkynyliodonium salts affords alkenylchlorozirconocenes with the Zr-C bond geminal to the iodonium moiety [176].…”

Section: Hydrozirconation Of Internal Alkynesmentioning

confidence: 99%

Hydrozirconation

Igau¹

2001

Catalytic Heterofunctionalization

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Stereospecific Synthesis of Temarotene, Its Structural Isomers, and Mixed Triaryl Alkenes from gem-Borazirconocene Alkenes

Cited by 37 publications

References 0 publications

Highly regio- and stereoselective synthesis of alkenylboronic esters by copper-catalyzed boron additions to disubstituted alkynes

Highly regio- and stereoselective synthesis of alkenylboronic esters by copper-catalyzed boron additions to disubstituted alkynes

Radical trans‐Hydroboration of Alkynes with N‐Heterocyclic Carbene Boranes

Hydrozirconation

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