167693-07-4

Upstream product

• 768-56-9 4-Phenylbut-1-ene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 73183-34-3 bis(pinacol)diborane 
• 1570511-19-1 2,2'-(4-phenylbutane-1,1-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) 
• 16520-62-0 4-Phenyl-1-butyne 
• 13633-25-5 1-Bromo-4-phenylbutane 
• 122-97-4 3-Phenyl-1-propanol 
• 3742-75-4 3-phenylpropyl 4-methylbenzenesulfonate 
• 78782-17-9 4,4,5,5-tetramethyl-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-1,3,2-dioxaborolane 
• 4119-41-9 1-iodo-3-phenylpropan 
• 637-59-2 1-Bromo-3-phenylpropane 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 4830-93-7 1-Chloro-4-phenylbutane 
• 104-53-0 3-phenyl-propionaldehyde 

Downstream Products

• 10521-91-2 5-phenylpentan-1-ol 
• 36329-86-9 (4-phenylbutyl)boronic acid 
• 36884-28-3 5-phenyl-1-pentanal 
• 20620-59-1 5-phenyl-n-valeric acid methyl ester 
• 3360-41-6 4-phenyl-butan-1-ol 

Relevant academic research and scientific papers

Synthesis of DBpin using Earth-abundant metal catalysis

The synthesis of DBpin was achieved using (EtBIP)CoCl2 or (tBuPNN)FeCl2 as pre-catalysts activated with NaOtBu. (EtBIP)CoCl2 was used as a pre-catalyst for the hydrogen isotope exchange of HBpin with D2, and (tBuPNN)FeCl2 for deuterogenolysis of B2pin2. The one-pot, tandem hydrogenolysis-hydroboration/deuterogenolysis-deuteroboration reaction of terminal alkenes could be catalysed by (tBuPNN)FeCl2 to give alkyl boronic esters.

Copper-Photocatalyzed Hydroboration of Alkynes and Alkenes

The photocatalytic hydroboration of alkenes and alkynes is reported. The use of newly-designed copper photocatalysts with B2Pin2 permits the formation a boryl radical, which is used for hydroboration of a large panel of alkenes and a

METHODS OF BORYLATION AND USES THEREOF

The present invention relates, in general terms, to methods of borylation and uses thereof. In particular, the present invention provides a method of borylating an alkene compound by contacting the compound with a boron compound, a Fe pre-catalyst and a protic additive. The borylation occurs at a vicinal (β) position to an electron donating or electron withdrawing moiety of the compound.

Photoinduced NaI-Promoted Radical Borylation of Alkyl Halides and Pseudohalides

A method for photoinduced NaI-promoted radical borylation of aliphatic halides and pseudohalides with bis(catecholato)diboron (B2cat2) as the boron source is introduced. The borylation reaction is operationally simple and shows high

Matteson Reaction under Flow Conditions: Iterative Homologations of Terpenes

The Matteson reaction is ideally suited for flow chemistry since it allows iterative homologation of boronate esters. The present study provides accurate data on reaction times of the individual steps of the Matteson reaction, which occurs in less than 10 s in total. The protocol allows terpenes to be (per-)homologated in a controlled manner to yield homo-, bishomo-, and trishomo-terpenols after oxidative workup. The new terpene alcohols are validated with respect to their olfactoric properties.

Preparation method of alkyl boride

The invention discloses a preparation method of alkyl boride. According to the method, alkyl halides (I, Br) and 2, 2 '-biphenyl [D] [1, 3, 2] dioxaborole (B2cat2) are used as raw materials, a properamount of electrolyte (optionally) is added, and the cor

Electrochemical Borylation of Alkyl Halides: Fast, Scalable Access to Alkyl Boronic Esters

Herein, a fast, scalable, and transition-metal-free borylation of alkyl halides (X = I, Br, Cl) enabled by electroreduction is reported. This process provides an efficient and practical access to primary, secondary, and tertiary boronic esters at a high current. More than 70 examples, including the late-stage borylation of natural products and drug derivatives, are furnished at room temperature, thereby demonstrating the broad utility and functional-group tolerance of this protocol. Mechanistic studies disclosed that B2cat2 serves as both a reagent and a cathodic mediator, enabling electroreduction of difficult-to-reduce alkyl bromides or chlorides at a low potential.

Enantioselective Cobalt-Catalyzed Cascade Hydrosilylation and Hydroboration of Alkynes to Access Enantioenriched 1,1-Silylboryl Alkanes

Enantioenriched 1,1-silylboryl alkanes possess silyl and boryl groups that are both connected to the same stereogenic carbon center at well-defined orientations. As these chiral multifunctionalized compounds potentially offer two synthetic handles, they are highly valued building blocks in asymmetric synthesis as well as medicinal chemistry. Despite the potential usefulness, efficient synthetic approaches for their preparation are scarce. Seeking to address this deficiency, an enantioselective cobalt-catalyzed hydrosilylation/hydroboration cascade of terminal alkynes has been realized. This protocol constitutes an impressive case of chemo-, regio-, and stereoselectivity wherein the two different hydrofunctionalization events are exquisitely controlled by a single set of metal catalyst and ligand, an operation which would usually require two separate catalytic systems. Downstream transformations of enantioenriched 1,1-silyboryl alkanes led to various valuable chiral compounds. Mechanistic studies suggest that the present reaction undergoes highly regioselective and stereocontrolled sequential hydrosilylation and hydroboration processes.

A Copper(I)-Catalyzed Radical-Relay Reaction Enabling the Intermolecular 1,2-Alkylborylation of Unactivated Olefins

The first catalytic intermolecular 1,2-alkylborylation reaction via a radical-relay mechanism between unactivated olefins, bis(pinacolato)diboron, and an alkyl electrophile is reported. Successful implementation of this method requires that the competing boryl substitution of the alkyl electrophile is retarded to facilitate the radical relay. This challenge was overcome using electronically or sterically demanding alkyl electrophiles, which results in the simultaneous and highly regioselective introduction of a gem-difluoro, monofluoro, tertiary, or secondary alkyl group and a boryl group across the C=C double bond.

Hydroboration of Terminal Alkenes and trans-1,2-Diboration of Terminal Alkynes Catalyzed by a Manganese(I) Alkyl Complex

A MnI-catalyzed hydroboration of terminal alkenes and a 1,2-diboration of terminal alkynes with pinacolborane (HBPin) is described. For alkenes, anti-Markovnikov hydroboration takes place; for alkynes the reaction proceeds with excellent trans-1,2-selectivity. The most active pre-catalyst is bench-stable alkyl bisphosphine MnI complex fac-[Mn(dippe)(CO)3(CH2CH2CH3)]. The catalytic process is initiated by migratory insertion of a CO ligand into the Mn–alkyl bond to yield an acyl intermediate, which undergoes B?H bond cleavage of HBPin (for alkenes) and rapid C?H bond cleavage (for alkynes), forming the active MnI boryl and acetylide catalysts [Mn(dippe)(CO)2(BPin)] and [Mn(dippe)(CO)2(C≡CR)], respectively. A broad variety of aromatic and aliphatic alkenes and alkynes was efficiently and selectively borylated. Mechanistic insights are provided based on experimental data and DFT calculations revealing that an acceptorless reaction is operating involving dihydrogen release.