480425-30-7

Usage

Uses

TRANS-2-(4-(TERT-BUTYLDIMETHYLSILYLOXY)& is used as a substrate in the field of organic chemistry for various applications due to its unique reactivity and properties.
Used in Catalyst-Free Zweifel Olefination:
In the catalyst-free Zweifel olefination of alkenyl boronic esters using triorganocerium reagents, TRANS-2-(4-(TERT-BUTYLDIMETHYLSILYLOXY)& is used as a substrate to facilitate the formation of alkenes. This reaction is significant in the synthesis of complex organic molecules and pharmaceutical compounds.
Used in Carbosulfenylation Reactions:
TRANS-2-(4-(TERT-BUTYLDIMETHYLSILYLOXY)& is also utilized in the study of carbosulfenylation reactions of alkenylboronates. These reactions are important for the synthesis of sulfur-containing compounds, which have various applications in the pharmaceutical and chemical industries.
Used in the Preparation of Chiral Tris(boronates):
TRANS-2-(4-(TERT-BUTYLDIMETHYLSILYLOXY)& is used to prepare chiral tris(boronates), which are essential building blocks for synthesizing challenging compounds. Chiral tris(boronates) are valuable in the development of enantiomerically pure molecules, which are crucial in the pharmaceutical industry for the production of drugs with specific biological activities.

InChI:InChI=1/C16H33BO3Si/c1-14(2,3)21(8,9)18-13-11-10-12-17-19-15(4,5)16(6,7)20-17/h10,12H,11,13H2,1-9H3/b12-10+

Upstream product

• 78592-82-2 4-(tert-butyldimethylsilyloxy)-1-butyne 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 73183-34-3 bis(pinacol)diborane 
• 108794-10-1 4-[(tert-butyldimethylsilyl)oxy]-1-butene 

Downstream Products

• 1429204-37-4 (E)-tert-butyl-(4-(3,4-dichlorophenyl)but-3-enyloxy)dimethylsilane 
• 1197880-39-9 3-{4-[(E)-4-(tert-butyl-dimethyl-silanoxy)-but-1-enyl]-benzyl}-2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridine 
• 923583-90-8 (E)-5-(4-(tert-butyldimethylsilyloxy)but-1-enyl)-3-(1-methyl-1H-pyrazol-4-yl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine 

Relevant academic research and scientific papers

Creating High Regioselectivity by Electronic Metal-Support Interaction of a Single-Atomic-Site Catalyst

Ligands are the most commonly used means to control the regioselectivity of organic reactions. It is very important to develop new regioselective control methods for organic synthesis. In this study, we designed and synthesized a single-atomic-site catalyst (SAC), namely, Cu1-TiC, with strong electronic metal-support interaction (EMSI) effects by studying various reaction mechanisms. π cloud back-donation to the alkyne on the metal catalytic intermediate was enhanced during the reaction by using transient electron-rich characteristics. In this way, the reaction achieved highly linear-E-type regioselective conversion of electronically unbiased alkynes and completely avoided the formation of branched isomers (ln:br >100:1, TON up to 612, 3 times higher than previously recorded). The structural elements of the SACs were designed following the requirements of the synthesis mechanism. Every element in the catalyst played an important role in the synthesis mechanism. This demonstrated that the EMSI, which is normally thought to be responsible for the improvement in catalytic efficiency and durability in heterogeneous catalysis, now first shows exciting potential for regulating the regioselectivity in homogeneous catalysis.

Zwitterion-Initiated Hydroboration of Alkynes and Styrene

The hydroboration of alkynes and styrene with HBpin has been developed using tris(pentaflurophenyl)borane (B(C6F5)3) as the initiator of catalysis. The hydroboration is proposed to be initiated by Lewis acid activation of the alkyne by (B(C6F5)3) to form a highly reactive zwitterionic species which subsequently react with HBpin to give the alkenyl boronic ester. This zwitterion has also showed potential to be a competent catalyst for the hydroboration of styrene. The zwitterionic intermediate is analogous to that proposed in the Piers borane-catalysed hydroboration and 1,1-carboboration of alkynes with B(C6F5)3. (Figure presented.).

Cobalt-Catalyzed Hydroboration of Terminal and Internal Alkynes

A novel methodology to access synthetically versatile vinylboronic esters through a ligand-controlled cobalt-catalyzed hydroboration of terminal and internal alkynes is reported. The approach relies on the in situ reduction of Co(II) by H-BPin in the presence of bisphosphine ligands generating catalytically active Co(I) hydride complexes. This procedure avoids the use of stoichiometric amounts of base, and no boron-containing byproducts are generated which is translated into high functional group tolerance and atom economy.

Nickel-Catalyzed Regioselective Hydroalkylation and Hydroarylation of Alkenyl Boronic Esters

Metal hydride catalyzed hydrocarbonation reactions of alkenes are an efficient approach to construct new carbon–carbon bonds from readily available alkenes. However, the regioselectivity of hydrocarbonation remains challenging to be controlled. In nickel hydride (NiH) catalyzed hydrocarbonation, linear selectivity is most often obtained because of the relative stability of the linear Ni–alkyl intermediate over its branched counterpart. Herein, we show that the boronic pinacol ester (Bpin) group directs a Ni-catalyzed hydrocarbonation to occur at its adjacent carbon center, resulting in formal branch selectivity. Both alkyl and aryl halides can be used as electrophiles in this hydrocarbonation, providing access to a wide range of secondary alkyl Bpin derivatives, which are valuable building blocks in synthetic chemistry. The utility of the method is demonstrated by the late-stage functionalization of natural products and drug molecules, the synthesis of an anticancer agent, and iterative syntheses.

Kinetics and Mechanism of the Arase-Hoshi R2BH-Catalyzed Alkyne Hydroboration: Alkenylboronate Generation via B-H/C-B Metathesis

The mechanism of R2BH-catalyzed hydroboration of alkynes by 1,3,2-dioxaborolanes has been investigated by in situ 19F NMR spectroscopy, kinetic simulation, isotope entrainment, single-turnover labeling (10B/2H), and density functional theory (DFT) calculations. For the Cy2BH-catalyzed hydroboration 4-fluorophenylacetylene by pinacolborane, the resting state is the anti-Markovnikov addition product ArCH = CHBCy2. Irreversible and turnover-rate limiting reaction with pinacolborane (k ≈ 7 × 10-3 M-1 s-1) regenerates Cy2BH and releases E-Ar-CH═CHBpin. Two irreversible events proceed in concert with turnover. The first is a Markovnikov hydroboration leading to regioisomeric Ar-C(Bpin)═CH2. This is unreactive to pinacolborane at ambient temperature, resulting in catalyst inhibition every ～102 turnovers. The second is hydroboration of the alkenylboronate to give ArCH2CH(BCy2)Bpin, again leading to catalyst inhibition. 9-BBN behaves analogously to Cy2BH, but with higher anti-Markovnikov selectivity, a lower barrier to secondary hydroboration, and overall lower efficiency. The key process for turnover is B-H/C-B metathesis, proceeding by stereospecific transfer of the E-alkenyl group within a transient, μ-B-H-B bridged, 2-electron-3-center bonded B-C-B intermediate.

Rhodium-catalyzed dehydrogenative borylation of aliphatic terminal alkenes with pinacolborane

Aliphatic terminal alkenes react with pinacolborane at ambient temperature to afford dehydrogenative borylation compounds as the major product when iPr-Foxap is used as the ligand with cationic rhodium(I) in the presence of norbornene, which acts as the s

Silver-catalyzed highly regioselective formal hydroboration of alkynes

A silver(I)-N-heterocyclic carbene complex has proven to be a potent catalyst for formal hydroboration of alkynes, providing a variety of borylalkenes in regio- and stereoselective manners. Under the silver catalysis, allenes also undergo regioselective hydroboration to give borylalkenes.

Stereoselective synthesis of (E)-vinylboronic esters via a Zr mediated hydroboration of alkynes

There is herein provided a process for Zr-mediated hydroboration of alkynes which offers (E)-vinylboronic esters in high yield with stereoselectivity and regioselectivity.

Zr-Mediated hydroboration: Stereoselective synthesis of vinyl boronic esters

An improved process for the preparation of (E)-vinylboronic esters via a Zr-mediated hydroboration of alkynes, especially oxygen-containing alkynes, is described.