Experimental and theoretical rationalization on regioselective mixed diboration of alkenes, with the unsymmetrical diboron reagent Bpin-Bdan, providing the protecting Bdan moiety in the internal position.
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The NaOBu-catalyzed mixed 1,1-diboration of terminal alkynes using the unsymmetrical diboron reagent BpinBdan (pin = pinacolato; dan = 1,8-diaminonaphthalene) proceeds in a regio- and stereoselective fashion affording moderate to high yields of 1,1-diborylalkenes bearing orthogonal boron protecting groups. It is applicable to gram-scale synthesis without loss of yield or selectivity. The mixed 1,1-diborylalkene products can be utilized in Suzuki-Miyaura cross-coupling reactions which take place selectivly at the C-B site.
View Article and Find Full Text PDFMixed Diboration of Alkynes Catalyzed by LiOH: Regio- and Stereoselective Synthesis of cis-1,2-Diborylalkenes.
Org Lett
December 2018
State Key laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis , Shanghai Institute of Organic Chemistry , University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road , Shanghai 200032 , China.
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.
View Article and Find Full Text PDFSubstrate-Assisted, Transition-Metal-Free Diboration of Alkynamides with Mixed Diboron: Regio- and Stereoselective Access to trans-1,2-Vinyldiboronates.
Angew Chem Int Ed Engl
April 2017
Department of Chemistry, Virginia Tech, 900 West Campus Drive, Blacksburg, VA, 24061, USA.
A substrate-assisted diboration of alkynamides using the unsymmetrical pinacolato-1,8-diaminonaphthalenato diboron (pinBBdan) is described. The transition-metal-free reaction proceeds in a regio- and stereoselective fashion to exclusively afford trans-vinyldiboronates in good to excellent yields. Notably, Bdan and Bpin are installed on the α- and β-carbon atoms, respectively.
View Article and Find Full Text PDFUnsymmetrical 1,1-diborated multisubstituted sp(3)-carbons formed via a metal-free concerted-asynchronous mechanism.
Org Biomol Chem
October 2015
Department Química Física i Inorgànica, University Rovira i Virgili, C/Marcel lí Domingo s/n, Tarragona, Spain.
We have experimentally proved the unsymmetrical 1,1-diboration of diazo compounds, formed in situ from aldehydes and cyclic and non-cyclic ketones, in the absence of any transition metal complex. The heterolytic cleavage of the mixed diboron reagent, Bpin-Bdan, and the formation of two geminal C-Bpin and C-Bdan bonds has been rationalised based on DFT calculations to occur via a concerted-asynchronous mechanism. Diastereoselection is attained on substituted cyclohexanones and DFT studies provide understanding on the origin of the selectivity.
View Article and Find Full Text PDFMixed diboration of alkenes in a metal-free context.
Chem Commun (Camb)
January 2015
Department Química Física i Inorgànica, University Rovira i Virgili, C/Marcel·lí Domingo s/n, Tarragona, Spain.
Experimental and theoretical rationalization on regioselective mixed diboration of alkenes, with the unsymmetrical diboron reagent Bpin-Bdan, providing the protecting Bdan moiety in the internal position.
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