An “On?Demand”, Selective Dehydrogenative Borylation or Hydroboration of Terminal Alkynes Using Zn ²⁺ ?based Catalyst

Copper-catalyzed dehydrogenative borylation of terminal alkynes with pinacolborane.

LCuOTf complexes [L = cyclic (alkyl)(amino)carbenes (CAACs) or N-heterocyclic carbenes (NHCs)] selectively promote the dehydrogenative borylation of C(sp)-H bonds at room temperature. It is shown that σ,π-bis(copper) acetylide and copper hydride complexes are the key catalytic species.

Rhodium-Catalyzed Dehydrogenative Borylation of Aliphatic Terminal Alkenes with Pinacolborane.

Aliphatic terminal alkenes react with pinacolborane at ambient temperature to afford dehydrogenative borylation compounds as the major product when iPr-Foxap is used as the ligand with cationic rhodium(I) in the presence of norbornene, which acts as the sacrificial hydrogen acceptor. The reaction is applied to the one-pot syntheses of aldehydes and homoallylic alcohols from aliphatic terminal a...

Rhodium-catalyzed dehydrogenative borylation of cyclic alkenes.

A rhodium-catalyzed dehydrogenative borylation of cyclic alkenes is described. This reaction provides direct access to cyclic 1-alkenylboronic acid pinacol esters, useful intermediates in organic synthesis. Suzuki-Miyaura cross-coupling applications are also presented.

Catalyst Development for Selective Hydrogenation of Functionalized Alkynes and Nitroarenes

Copper-catalyzed dehydrogenative borylation of terminal alkynes with pinacolborane† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c6sc02668k Click here for additional data file.

A. General Considerations ................................................................................................................................2 B. Optimization Tables for the Dehydroborylation Reaction............................................................2 C. Catalytic procedure for the Dehydroborylation Reaction .............................................................3 D...