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Statements

Subject Item
n2:RIV%2F60461373%3A22310%2F09%3A00021602%21RIV10-MSM-22310___
rdf:type
skos:Concept n18:Vysledek
dcterms:description
Contrary to all previous reports, bromoboration of propyne with BBr3 proceeds in >= 98% syn-selectivity to produce (Z)-2-bromo-1-propenyldibromoborane (1). Although 1 is readily prone to stereoisomerization, it can be converted to the pinacolboronate (2) of >= 98% isomeric purity by treatment with pinacol, which may then be subjected to Negishi coupling to give trisubstituted (Z)-alkenylpinacolboronates (3) containing various R groups in 73-90% yields. Iodinolysis of 3 affords alkenyl iodides (4) in 80-90% yields. All alkenes isolated and identified are >= 98% Z Contrary to all previous reports, bromoboration of propyne with BBr3 proceeds in >= 98% syn-selectivity to produce (Z)-2-bromo-1-propenyldibromoborane (1). Although 1 is readily prone to stereoisomerization, it can be converted to the pinacolboronate (2) of >= 98% isomeric purity by treatment with pinacol, which may then be subjected to Negishi coupling to give trisubstituted (Z)-alkenylpinacolboronates (3) containing various R groups in 73-90% yields. Iodinolysis of 3 affords alkenyl iodides (4) in 80-90% yields. All alkenes isolated and identified are >= 98% Z
dcterms:title
Highly Regio- and Stereoselective Synthesis of (Z)-Trisubstituted Alkenes via Propyne Bromoboration and Tandem Pd-Catalyzed Cross-Coupling Highly Regio- and Stereoselective Synthesis of (Z)-Trisubstituted Alkenes via Propyne Bromoboration and Tandem Pd-Catalyzed Cross-Coupling
skos:prefLabel
Highly Regio- and Stereoselective Synthesis of (Z)-Trisubstituted Alkenes via Propyne Bromoboration and Tandem Pd-Catalyzed Cross-Coupling Highly Regio- and Stereoselective Synthesis of (Z)-Trisubstituted Alkenes via Propyne Bromoboration and Tandem Pd-Catalyzed Cross-Coupling
skos:notation
RIV/60461373:22310/09:00021602!RIV10-MSM-22310___
n3:aktivita
n17:S n17:Z
n3:aktivity
S, Z(MSM 223100001)
n3:cisloPeriodika
18
n3:dodaniDat
n7:2010
n3:domaciTvurceVysledku
n12:6702198
n3:druhVysledku
n15:J
n3:duvernostUdaju
n5:S
n3:entitaPredkladatele
n16:predkladatel
n3:idSjednocenehoVysledku
317159
n3:idVysledku
RIV/60461373:22310/09:00021602
n3:jazykVysledku
n14:eng
n3:klicovaSlova
ETHERATE MEDIATED 1,4-ADDITION; CARBON BOND FORMATION; ORGANIC-SYNTHESIS; HALOBORATION REACTION; STEREOSPECIFIC SYNTHESIS; REGIOSELECTIVE SYNTHESIS; TERMINAL ALKYNES; CONTROLLED CARBOMETALATION; DERIVATIVES; ALCOHOLS
n3:klicoveSlovo
n8:CARBON%20BOND%20FORMATION n8:REGIOSELECTIVE%20SYNTHESIS n8:DERIVATIVES n8:TERMINAL%20ALKYNES n8:HALOBORATION%20REACTION n8:4-ADDITION n8:ORGANIC-SYNTHESIS n8:ALCOHOLS n8:ETHERATE%20MEDIATED%201 n8:CONTROLLED%20CARBOMETALATION n8:STEREOSPECIFIC%20SYNTHESIS
n3:kodStatuVydavatele
US - Spojené státy americké
n3:kontrolniKodProRIV
[D285549D3E8D]
n3:nazevZdroje
Organic Letters
n3:obor
n13:CC
n3:pocetDomacichTvurcuVysledku
1
n3:pocetTvurcuVysledku
4
n3:rokUplatneniVysledku
n7:2009
n3:tvurceVysledku
Wang, Chao Tobrman, Tomáš Xu, Zhaoqing Negishi, Ei-Ichi
n3:wos
000269670700017
n3:zamer
n10:MSM%20223100001
s:issn
1523-7060
s:numberOfPages
4
n11:organizacniJednotka
22310