815575-36-1

Upstream product

• 917-92-0 3,3-Dimethylbut-1-yne 
• 73183-34-3 bis(pinacol)diborane 

Downstream Products

• 1391743-04-6 (E)-2-(3,3-dimethyl-1-(p-tolyl)but-1-en-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 31612-63-2 (2S)-3,3-dimethylbutane-1,2-diol 

Relevant academic research and scientific papers

Base-catalyzed diborylation of alkynes: synthesis and applications of cis-1,2-bis(boryl)alkenes

An efficient, transition-metal free, and practical approach to cis-bis(boryl)alkenes from various alkynes was disclosed in the presence of a catalytic amount of K2CO3 under mild conditions. Meanwhile, tetrasubstituted alkenes and phenanthrene derivatives were readily constructed from the target diborylalkenes via Suzuki-Miyaura cross coupling.

Mixed Diboration of Alkynes Catalyzed by LiOH: Regio- and Stereoselective Synthesis of cis-1,2-Diborylalkenes

A diboration of terminal alkynes with an unsymmetrical diboron reagent pinBBdan has been achieved using LiOH as the catalyst in the presence of stoichiometric amounts of MeOH, affording 1,2-diborylalkenes with different boryl groups. The reaction proceeds in a highly regio- and stereoselective manner through cis-addition of pinBBdan to the C-C triple bond, with the Bdan moiety being incorporated at the internal position. By taking advantage of the different reactivities of the two boryl groups, the mixed diboration product can undergo the sequential, chemoselective cross-couplings with aryl bromides to form trisubstituted alkenes.

Solvent-and ligand-free diboration of alkynes and alkenes catalyzed by platinum nanoparticles on titania

Platinum nanoparticles supported on titania efficiently catalyzed the diboration of alkynes and alkenes under solvent-and ligand-free conditions in air. The cis-1,2-diborylalkenes and 1,2-diborylalkanes were obtained in moderate to excellent yields following, in most cases, a simple filtration workup protocol. The versatility of the cis-1,2-diboronvinyl compounds was demonstrated in a series of organic transformations, including the Suzuki-Miyaura cross coupling and the boron-halogen exchange. Click diboration: The diboration of alkynes and alkenes catalyzed by platinum nanoparticles on titania is shown to take place under solvent-and ligand-free conditions in air. The 1,2-diboronvinyl compounds are obtained with exclusive cis stereochemistry and are subjected to different useful chemical transformations.

Iridium-catalyzed enantioselective hydrogenation of alkenylboronic esters

Choose the right ligand: An iridium complex derived from a phosphino-imidazoline ligand is a highly efficient catalyst for the asymmetric hydrogenation of terminal vinyl boronic esters (see scheme). On the other hand, trisubstituted alkenyl-boronates can

Catalytic enantioselective hydrogenation of vinyl bis(boronates)

Catalytic enantioselective hydrogenation of prochiral vinylmetallic reagents can provide an attractive alternative to hydrometalation and bismetalation of alkenes. In this contribution, the first highly enantioselective hydrogenation of vinyl boronic esters is described. The chiral reduction products are versatile intermediates for chemical synthesis. Copyright