"000269670700017" . "1523-7060" . "4"^^ . . "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" . . "RIV/60461373:22310/09:00021602" . "4"^^ . . "1"^^ . "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"@en . . "RIV/60461373:22310/09:00021602!RIV10-MSM-22310___" . "Wang, Chao" . . "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"@en . "Organic Letters" . "S, Z(MSM 223100001)" . . "22310" . "Tobrman, Tom\u00E1\u0161" . . "Highly Regio- and Stereoselective Synthesis of (Z)-Trisubstituted Alkenes via Propyne Bromoboration and Tandem Pd-Catalyzed Cross-Coupling" . . . . . . . "Xu, Zhaoqing" . . "18" . "ETHERATE MEDIATED 1,4-ADDITION; CARBON BOND FORMATION; ORGANIC-SYNTHESIS; HALOBORATION REACTION; STEREOSPECIFIC SYNTHESIS; REGIOSELECTIVE SYNTHESIS; TERMINAL ALKYNES; CONTROLLED CARBOMETALATION; DERIVATIVES; ALCOHOLS"@en . . . . . . . "Negishi, Ei-Ichi" . "Highly Regio- and Stereoselective Synthesis of (Z)-Trisubstituted Alkenes via Propyne Bromoboration and Tandem Pd-Catalyzed Cross-Coupling"@en . "[D285549D3E8D]" . "US - Spojen\u00E9 st\u00E1ty americk\u00E9" . "317159" . . . .