62072-25-7Relevant academic research and scientific papers
Capturing HBCy2: Using N,O-Chelated Complexes of Rhodium(I) and Iridium(I) for Chemoselective Hydroboration
Drover, Marcus W.,Schafer, Laurel L.,Love, Jennifer A.
supporting information, p. 3181 - 3186 (2016/03/12)
1,3-N,O-chelated complexes of RhI and IrI cooperatively and reversibly stabilized the B-H bond of HBCy2 to afford six-membered metallaheterocycles (M=Rh (7) or Ir (8)) having a δ-[M]?H-B agostic interaction. Treatment of these Shimoi-type borane adducts 7 or 8 with both an aldehyde and an alkene resulted in chemoselective aldehyde hydroboration and reformation of the 1,3-N,O-chelated starting material. The observed chemoselectivity is inverted from that of free HBCy2, which is selective for alkene hydroboration.
3-Chloro-1-lithiopropene, a functional organolithium reagent, and its reactions with alkylboronates to give 3-alkylprop-1-en-3-ols
Smith, Keith,Elliott, Mark C.,Jones, D. Heulyn
, p. 9526 - 9531 (2013/10/08)
The reagent 3-chloro-1-lithiopropene (4) can be generated by treating 1-bromo-3-chloropropene with t-BuLi. It is unstable but if generated at low temperature in the presence of alkylboronic esters, such as 3, is trapped in situ to give rearrangement products 2, which on oxidation give 3-alkylprop-1-en-3-ols in good yields. The reaction works for primary, secondary, benzylic, and even tertiary alkylboronic esters, providing allylic alcohols bearing almost any alkyl group available using organoborane chemistry and incorporating all features of such groups.
Construction of terminal conjugated enynes: Cu-mediated cross-coupling reaction of alkenyldialkylborane with (trimethylsilyl)ethynyl bromide
Hoshi, Masayuki,Kawamura, Noritsugu,Shirakawa, Kazuya
, p. 1961 - 1970 (2007/10/03)
The cross-coupling reaction of (E)- and (Z)-alk-1-enyldialkylborane with (trimethylsilyl)ethynyl bromide proceeds in the presence of a catalytic amount of copper(II) acetylacetonate and a base under extremely mild conditions to provide conjugated enynes w
A one-pot diastereoselective synthesis of cis-3-hexene-1,6-diols via an unusually reactive organozinc intermediate
Garcia, Celina,Libra, Eric R.,Carroll, Patrick J.,Walsh, Patrick J.
, p. 3210 - 3211 (2007/10/03)
A highly diastereoselective method for the synthesis of cis-3-hexene-1,6-diols has been developed. This new reaction proceeds with excellent control of diastereoselectivity over four stereocenters and the double bond geometry. The diols are made in a one-pot procedure involving hydroboration of a terminal alkyne and transmetalation to zinc to give a divinylzinc intermediate. This intermediate undergoes reductive elimination, forming a C=C bond. In the absence of a trapping reagent, diene is liberated (70% yield); however, in the presence of ketones or aldehydes, the proposed intermediate metallocyclopentene is trapped via a double insertion of the carbonyl substrate. Workup provides the diols in 47-86% yield. Copyright
Stereoselective synthesis of E-vinylteIIurides via boron-tellurium exchange
Huang, Xian,Liang, Chun-Gen
, p. 2625 - 2626 (2007/10/03)
E-Alkenylboranes reacted with diorgano ditellurides in the presence of a palladium complex to afford E-vinyltelluridesstereoselectively. The Royal Society of Chemistry 1999.
Stereoselective dehalogenation of (Z)-1-halo-1-alkenyldialkylborane with tributyltin hydride: The behavior of tributyltin hydride as a hydride donor
Hoshi, Masayuki,Takahata, Kimitomo,Arase, Akira
, p. 453 - 456 (2007/10/03)
The reaction of (Z)-1-halo-1-alkenyldialkylborane (1) with tributyltin hydride (n-Bu3SnH) at 0°C or room temperature results in reductive removal of the halogen atom to afford (E)- or (Z)-1-alkenyldialkylborane whose stereochemistry depends on the dialkylboryl group and the alkenyl group of 1.
