- Transborylation of alkenylboranes with diboranes
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Exchange of boryl moieties between alkenylboranes and diboron reagents has been postulated as a stereospecific cross-metathesis pathway with concomitant formation of mixed diboron reagents. DFT calculations propose a mechanism for the stereocontrolled C(sp2)-B/B′-B′ cross-metathesis with both symmetric and non-symmetric diboron reagents. This journal is
- Bru, Gerard,Carbó, Jorge J.,Dominguez-Molano, Paula,Fernández, Elena,Maza, Ricardo J.,Salvado, Oriol
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supporting information
p. 13361 - 13364
(2021/12/17)
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- Improved dimethylzinc-promoted vinylation of nitrones with vinylboronic esters
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Vinylboronic esters derived from 4,4,6-trimethyl-[1,3,2]dioxaborinane react with nitrones in the presence of dimethylzinc; nucleophilic addition of the vinyl group onto nitrones produces N-allylic hydroxylamines in fair yields. The sequence is compatible with various functional groups on the vinylic moiety. The mechanism and kinetic aspects are discussed on the basis of DFT calculations.
- Praveenganesh, Nageswaran,De Candia, Cristina,Memboeuf, Antony,Lendvay, Gy?rgy,Gimbert, Yves,Chavant, Pierre Y.
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scheme or table
p. 2447 - 2454
(2010/11/05)
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- A stereoselective synthesis of 1,6-diphenyl-1,3,5-hexatrienes utilising 4,4,6-trimethyl-2-vinyl-1,3,2-dioxaborinane as a two-carbon alkenyl building block
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A number of 1,6-diphenyl-1,3,5-hexatrienes of varying alkene geometries were stereoselectively prepared from just two starting materials: iodobenzene and 4,4,6-trimethyl-2-vinyl-1,3,2-dioxaborinane via a series of Heck, Suzuki-Miyaura and stereocontrolled iododeboronation reactions. These results demonstrate how 4,4,6-trimethyl-2-vinyl-1,3,2-dioxaborinane can be used as a genuine two-carbon vinyl-dianion building block in stereocontrolled polyene synthesis. The Royal Society of Chemistry 2005.
- Lightfoot, Andrew P.,Twiddle, Steven J.R.,Whiting, Andrew
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p. 3167 - 3172
(2007/10/03)
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- 4,4,6-Trimethyl-2-vinyl-1,3,2-dioxaborinane: A superior 2-carbon building block for vinylboronate Heck couplings
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4,4,6-Trimethyl-2-vinyl-1,3,2-dioxaborinane is a superior reagent in terms of stability and reactivity in comparison to the vinylboronate pinacol ester, giving improved selectivity for Heck versus Suzuki coupling with both aryl iodides and bromides, and being easier to prepare and store.
- Lightfoot, Andrew P.,Maw, Graham,Thirsk, Carl,Twiddle, Steven J. R.,Whiting, Andrew
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p. 7645 - 7648
(2007/10/03)
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