90408-77-8

Upstream product

• 766-46-1 2-bromo-1-ethynylbenzene 
• 6630-33-7 ortho-bromobenzaldehyde 
• 54321-62-9 (2-bromophenyl)methanol-d₁ 
• 59151-16-5 2-bromobenzaldehyde-α-d₁ 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 2039-88-5 2-bromostyrene 

Downstream Products

• 1211481-15-0 2-allyl-N-[2-(1-deuteriovinyl)phenyl]aniline 
• 1601464-37-2 trimethyl[(2-vinylphenyl)ethynyl]silane-d1 
• 1601463-97-1 C₁₀H₇⁽²⁾H 
• 1601464-00-9 2-(2-vinylphenyl)-1,8b-dihydrobiphenylene-d2 

Relevant academic research and scientific papers

Direct access to substituted benzo[b] carbazoles through cascade annulation of 2-vinylbenzaldehydes with indoles

A highly efficient palladium-catalyzed cascade annulation of 2-vinylbenzaldehydes with indoles has been achieved to afford 6-(3-indolyl)benzo[b]carbazoles under mild conditions in good yield and with excellent regioselectivity. Mechanistic investigations reveal that the reaction proceeds via double addition of indoles, unexpected intramolecular 1,4-aryl and 1,2-hydrogen migrations, and oxidative aromatization.

Catalytic α-Selective Deuteration of Styrene Derivatives

We report an operationally simple protocol for the catalytic α-deuteration of styrenes. This process proceeds via the base-catalyzed reversible addition of methanol to styrenes in DMSO-d6 solvent. The concentration of methanol is shown to be critical for high yields and selectivities over multiple competing side reactions. The synthetic utility of α-deuterated styrenes for accessing deuterium-labeled chiral benzylic stereocenters is demonstrated.

Unlocking Mizoroki–Heck-Type Reactions of Aryl Cyanides Using Transfer Hydrocyanation as a Turnover-Enabling Step

A new transfer hydrofunctionalization strategy to turnover H-MII-X complexes has enabled both intra- and intermolecular Mizoroki–Heck (MH)-type reactions of aryl cyanides that are challenging to realize under traditional, basic conditions. Initially, a cascade carbonickelation/MH reaction of 2-cyanostyrenes was achieved using a key alkyne transfer hydrocyanation step. Mechanistic experiments supported the proposed catalytic cycle, including the turnover-enabling transfer hydrocyanation step. The reactivity was then extended to the intermolecular MH reaction of benzonitriles and styrenes.

Dihydrobiphenylenes through ruthenium-catalyzed [2+2+2] cycloadditions of ortho-alkenylarylacetylenes with alkynes

A new synthetic route to dihydrobiphenylenes has been developed. The process involves a mild RuII-catalyzed [2+2+2] dimerization of ortho-alkenylarylacetylenes or its more versatile variant, the Ru-catalyzed [2+2+2] cycloaddition of ortho-ethynylstyrenes with alkynes. Mechanistic aspects of this [2+2+2] cycloaddition are discussed. A new synthetic route to dihydrobiphenylenes involves a mild RuII-catalyzed [2+2+2] dimerization of ortho-alkenylarylacetylenes or its more versatile variant, the Ru-catalyzed [2+2+2] cycloaddition of ortho-ethynylstyrenes with alkynes. The mechanistic aspects of this [2+2+2] cycloaddition are also discussed. Copyright

α-Selective Ni-catalyzed hydroalumination of aryl- and alkyl-substituted terminal alkynes: Practical syntheses of internal vinyl aluminums, halides, or boronates

A method for Ni-catalyzed hydroalumination of terminal alkynes, leading to the formation of α-vinylaluminum isomers efficiently (>98% conv in 2-12 h) and with high selectivity (95% to >98% α), is described. Catalytic α-selective hydroalumination reactions proceed in the presence of a reagent (diisobutylaluminum hydride; dibal-H) and 3.0 mol % metal complex (Ni(dppp)Cl2) that are commercially available and inexpensive. Under the same conditions, but with Ni(PPh3)2Cl2, hydroalumination becomes highly β-selective, and, unlike uncatalyzed transformations with dibal-H, generates little or no alkynylaluminum byproducts. All hydrometalation reactions are reliable, operationally simple, and practical and afford an assortment of vinylaluminums that are otherwise not easily accessible. The derived α-vinyl halides and boronates can be synthesized through direct treatment with the appropriate electrophiles [e.g., Br 2 and methoxy(pinacolato)boron, respectively]. Ni-catalyzed hydroaluminations can be performed with as little as 0.1 mol % catalyst and on gram scale with equally high efficiency and selectivity.