Iron-Catalyzed Dehydrogenative Borylation of Terminal Alkynes

Duo Wei (1) , Bertrand Carboni (1) , Jean-Baptiste Sortais (1, 2, 3) , Christophe Darcel (1)

1 ISCR - Institut des Sciences Chimiques de Rennes
2 IUF - Institut Universitaire de France
3 LCC - Laboratoire de chimie de coordination

The catalytic system based on Fe(OTf)(2) (2.5 mol%) and DABCO (1 mol%) selectively promotes the dehydrogenative borylation of both aromatic and aliphatic terminal alkynes to afford alkynylboronate derivatives in the presence of 1 equiv. of pinacolborane at 100 degrees C in toluene. This methodology is applicable to a variety of terminal alkynes (16 examples, yield 62-93%).

Keywords: Iron; alkyne; dehydrogenative borylation; pinacolborane; alkynylboronates

Domains: Chemical Sciences; Organic chemistry; Chemical Sciences; Catalysis

Duo Wei, Bertrand Carboni, Jean-Baptiste Sortais, Christophe Darcel. Iron-Catalyzed Dehydrogenative Borylation of Terminal Alkynes. Advanced Synthesis and Catalysis, 2018, 360 (19), pp.3649-3654. ⟨10.1002/adsc.201800588⟩. ⟨hal-01902040⟩