| Identification | Back Directory | [Name]
(E)-1-Bromo-4-trimethylsilyl-1-buten-3-yne | [CAS]
107646-62-8 | [Synonyms]
(E)-1-Bromo-4-trimethylsilyl-1-buten-3-yne
(E)-(4-BROMOBUT-3-EN-1-YN-1-YL)TRIMETHYLSILANE
Silane, [(3E)-4-bromo-3-buten-1-yn-1-yl]trimethyl- | [Molecular Formula]
C7H11BrSi | [MDL Number]
MFCD17013477 | [MOL File]
107646-62-8.mol | [Molecular Weight]
203.15 |
| Chemical Properties | Back Directory | [Boiling point ]
164.5±19.0 °C(Predicted) | [density ]
1.195±0.06 g/cm3(Predicted) | [solubility ]
insoluble in water; soluble in hexane, ether, alcohol,
and most other organic solvents. |
| Hazard Information | Back Directory | [Physical properties]
bp 72–74°C/15mm-Hg; d 1.076 g cm?3. | [Uses]
(E)-1-Bromo-4-trimethylsilyl-1-buten-
3-yne can be as a Nucleophile in the Pd-Catalyzed Cross-Coupling.
Treatment of with t-BuLi (2.1 equiv) in Et2O at ?78°C followed
by addition of dry ZnBr2 (1 equiv) in THF at ?78 to
0°C generates in situ the corresponding alkenylzinc reagent.
Its Pd-catalyzed cross-coupling reaction provides an alternate
and complementary route to conjugated enynes and oligoenynes.
Thus, for example, a difunctional trienyne suitable for the synthesis
of 6,7-dehydrostipiamide (11) has been synthesized from
and (E)-BrCH=C(Me)COOEt in three steps in 75% overall
yield with complete control of regiochemistry and stereochemistry
(Scheme 5). | [Preparation]
obtained by the Pd(PPh3)4 catalyzed
cross-coupling reaction of (E)-1-bromo-2-iodoethylene with
TMS??≡≡??ZnBr generated in situ by the reaction of
TMS??≡≡, MeMgBr, and ZnBr2. |
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