Synthesis of Stereodefined 1,1-Diborylalkenes via Copper-Catalyzed Diboration of Terminal Alkynes.

ABSTRACT: A copper-catalyzed method for the E-selective 1,1-diboration of terminal alkynes is described. The tandem process involves sequential dehydrogenative borylation of the alkyne substrate with HBdan (1,8-diaminonaphthalatoborane), followed by hydroboration with HBpin (pinacolborane). This method proceeds efficiently under mild conditions, furnishing 1,1-diborylalkenes with excellent stereoselectivity and broad functional group tolerance. Taking advantage of the different reactivities of the two boryl moieties, the products can then be employed in stepwise cross-couplings with aryl halides for the stereocontrolled construction of trisubstituted alkenes.

SUBMITTER: Gao Y 

PROVIDER: S-EPMC7391966 | biostudies-literature | 2020 Jul

REPOSITORIES: biostudies-literature