77855-67-5

Upstream product

• 931-49-7 1-ethenylcyclohexene 
• 274-07-7 benzo[1,3,2]dioxaborole 
• 120-80-9 benzene-1,2-diol 

Downstream Products

• 77855-70-0 (1Z,3E)-1-phenyl-4-(1-cyclohexenyl)-1,3-butadiene 
• 245432-97-7 2-[(E)-2-(cyclohex-1-en-1-yl)ethenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 138375-81-2 [(E)-2-(cyclohex-1-en-1-yl)ethenyl]boronic acid 
• 109769-53-1 ((1Z,3E)-4-Cyclohex-1-enyl-2-methyl-buta-1,3-dienylsulfanyl)-benzene 

Relevant academic research and scientific papers

Syntheses with organoboranes. X. Monohydroboration of conjugated enynes with catecholborane catalyzed by nickel(II) chloride complexes with diphosphines

The monohydroboration of representative conjugated enynes - but-1-en-3-yne (1), 2-methylbut-1-en-3-yne (2), pent-3-en-1-yne (3), hex-1-en-3-yne (4), 2-methyl-4-phenyl-but-1-en-3-yne (5), 4-methyl-1-phenylpent-3-en-1-yne (6) and 1-ethynylcyclohex-1-ene (7)

Preparation of (E)-1-alkenylboronic acid pinacol esters via transfer of alkenyl group from boron to boron

Two synthetic routes to (E)-1-alkenylboronic acid pinacol esters 3 were investigated. Hydroboration of 1-alkynes 1 with 1,3,2-benzodioxaborole (catecholborane), in situ generated by the reaction of BH3 in THF with catechol, proceeded in the presence of a catalytic amount of dicyclohexylborane in THF at room temperature to give the corresponding (E)-1-alkenylboronic acid catechol esters 2. Treatment of the resultant esters 2 with 2,3-dimethyl-2,3-butanediol (pinacol) easily afforded the desired products 3, which are insensitive to air, moisture and chromatography, in good to high overall yields. The sequential reaction is a highly efficient route to 3 from BH3 in THF in a one-pot manner. Alternatively, hydroboration of 1 with 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (pinacolborane) was achieved in the presence of a catalytic amount of dicyclohexylborane at room temperature under neat conditions to afford the corresponding products 3 directly in good to excellent yields. This route is extremely efficient and environmentally benign from the viewpoints of making good use of pinacolborane and of using no solvent, and is capable of using a variety of alkynes 1 including functionalized ones such as HCCCH2Cl and HCCCH2OTHP.

Palladium catalysed tandem cyclisation-anion capture. Part 8: Cascade hydrostannylation-cyclisation-anion capture and cascade hydroboration-cyclisation-anion capture on solid phase

Up to four bonds and five stereocentres are created, in five component processes (five point diversity), utilising resin bound aryl iodides by hydroboration or hydrostannylation of alkynes, followed by cyclisation-anion capture involving Suzuki or Stille reactions. Three small libraries were prepared to validate the chemistry.