197313-32-9

Usage

InChI:InChI=1/C12H22BClO2/c1-11(2)12(3,4)16-13(15-11)9-7-5-6-8-10-14/h7,9H,5-6,8,10H2,1-4H3/b9-7+

Upstream product

• 10297-06-0 1-chloro-5-hexyne 
• 73183-34-3 bis(pinacol)diborane 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 

Downstream Products

• 1443734-85-7 benzyl (E)-8-chlorooct-3-enoate 
• 1453804-82-4 C₁₉H₂₀ClNO 
• 1218790-09-0 C₁₈H₃₄B₂O₄ 
• 25712-33-8 anti-cyclohexane-1,2-diyldimethanol 
• 57794-08-8 (1S,2S)-trans-1,2-Cyclohexanediol 
• 1072-86-2 (1R,2R)-trans-1,2-cyclohexanediol 

Relevant academic research and scientific papers

Hexamethyldisilazane Lithium (LiHMDS)-Promoted Hydroboration of Alkynes and Alkenes with Pinacolborane

Lithium-promoted hydroboration of alkynes and alkenes using commercially available hexamethyldisilazane lithium as a precatalyst and HBpin as a hydride source has been developed. This method will be appealing for organic synthesis because of its remarkable substrate tolerance and good yields. Mechanistic studies revealed that the hydroboration proceeds through the in situ-formed BH3species, which acts to drive the turnover of the hydroboration of alkynes and alkenes.

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.

Synthesis method of alkenyl boric acid ester

The invention discloses a synthesis method of alkenyl boric acid ester. The alkenyl boric acid ester compound with a diversified structure is obtained by catalyzing hydroboration of alkyne through rare earth. Particularly, the alkenyl boric acid ester com

Nickel-Catalyzed Highly Selective Hydroalkenylation of Alkenyl Boronic Esters to Access Allyl Boron

Allyl boron derivatives are valuable building blocks in the synthesis of natural products and bioactive molecules. Herein, a practical strategy of nickel-catalyzed highly selective hydroalkenylation of alkenyl boronic esters was developed. Under the mild

Reductive Cyclization of Unactivated Alkyl Chlorides with Tethered Alkenes under Visible-Light Photoredox Catalysis

The chemical inertness of abundant and commercially available alkyl chlorides precludes their widespread use as reactants in chemical transformations. Presented in this work is a metallaphotoredox methodology to achieve the catalytic intramolecular reductive cyclization of unactivated alkyl chlorides with tethered alkenes. The cleavage of strong C(sp3)?Cl bonds is mediated by a highly nucleophilic low-valent cobalt or nickel intermediate generated by visible-light photoredox reduction employing a copper photosensitizer. The high basicity and multidentate nature of the ligands are key to obtaining efficient metal catalysts for the functionalization of unactivated alkyl chlorides.

Silver-Catalyzed anti-Markovnikov Hydroboration of C-C Multiple Bonds

A simple silver salt (AgOAc)-catalyzed anti-Markovnikov-selective hydroboration of alkenes, 1,3-dienes, and alkynes with pinacolborane (HBpin) has been described. This strategy provides an efficient and practical method to access various alkyl-, allyl-, a

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.

Transition-metal-free hydroboration of terminal alkynes activated by base

Transition-metal and ligand-free method for the hydroboration of terminal alkynes with B2pin2 was reported in LiOt-Bu/toluene/MeOH system under room temperature. Alkylalkynes and arylalkynes reacted efficiently with high regioselecti

Lewis acid catalysis: Catalytic hydroboration of alkynes initiated by Piers' borane

Terminal and internal alkynes are efficiently hydroborated to (E)-alkenyl pinacol boronic esters with excellent yields and selectivities using a Lewis acid catalyst. In the case of Piers' borane (HB(C6F5)2) the borane acts as a pre-catalyst generating dissymmetrically gem-diborylated species of the form RCH2CR′(Bpin)(B(C6F5)2) which are the active catalysts.

Enantioselective synthesis of anti homoallylic alcohols from terminal alkynes and aldehydes based on concomitant use of a cationic iridium complex and a chiral phosphoric acid

We report a highly diastereo- and enantioselective synthesis of anti homoallylic alcohols from terminal alkynes via (E)-1-alkenylboronates based upon two catalytic reactions: a cationic iridium complex-catalyzed olefin transposition of (E)-1-alkenylboronates and a chiral phosphoric acid-catalyzed allylation reaction of aldehydes.