Mixed Diboration of Alkynes Catalyzed by LiOH: Regio- and Stereoselective Synthesis of cis-1,2-Diborylalkenes was written by Peng, Sihan;Liu, Guixia;Huang, Zheng. And the article was included in Organic Letters in 2018.Electric Literature of C16H20B2N2O2 This article mentions the following:
A diboration of terminal alkynes with an unsym. 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. In the experiment, the researchers used many compounds, for example, 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine (cas: 1214264-88-6Electric Literature of C16H20B2N2O2).
2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine (cas: 1214264-88-6) belongs to alcohols. Because alcohols are easily synthesized and easily transformed into other compounds, they serve as important intermediates in organic synthesis. Secondary alcohols are easily oxidized without breaking carbon-carbon bonds only as far as the ketone stage. No further oxidation is seen except under very stringent conditions.Electric Literature of C16H20B2N2O2
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts