Bis(pinacolato)diboron

Abstract

This feature focuses on a reagent chosen by a postgraduate, highlighting the uses and preparation of the reagent in current research 2442 SPOTLIGHT Bis(pinacolato)diboron Compiled by Xinyu Liu Xinyu Liu was born in Shenyang, China in 1978. He studied chemistry in Kyoto University, Japan and received his B.E. in 2002. From April 2001 to May 2003, he was a research student in the group of Prof. Tamejiro Hiyama, Kyoto University, where he worked on the synthetic applications of stereoselectively generated CF 3 -substituted lithio-oxirane. In June 2003, he moved to ETH-Zürich, Switzerland, and is currently working towards his Ph.D. degree under the supervision of Prof.

Diboron(4) Compounds: From Structural Curiosity to Synthetic Workhorse

“…Indeed, it is now difficult to keep pace with the latest developments using these tetraalkoxydiboron(4) compounds, including tetrahydroxydiboron, as their full potential is still coming to light (Figure ). − The volume of papers published in this area has grown exponentially, with bis­(pinacolato)­diboron appearing as a reactant or reagent in as many as 8193 publications (SciFinder, 01.02.2016). The utility of these remarkable compounds continues to grow rapidly, warranting this new review which details many of the recent developments in this evolving area.…”

Hydrogen Evolution from Telescoped Miyaura Borylation and Suzuki Couplings Utilizing Diboron Reagents: Process Safety and Hazard Considerations

“…Diboron coupling agents, bis­(pinacolato)­diboron (BisPin) and tetrahydroxy-diboron (bisboric acid or BBA) for example, have found wide utility as reagents in Miyaura borylation and Suzuki cross-coupling reactions, which are powerful reactions for the formation of carbon–carbon bonds. , Telescoping the two reactions together has been widely demonstrated, − often resulting in a streamlined process, the removal of additional unit operations associated with the isolation of the boronic ester, and a higher overall yield. The diboron reagent is often used in excess in borylation reactions to favor the desired reaction over the possibly competing Suzuki homocoupling of the aryl halide starting material and the formed boronate ester or to reduce reaction completion time in the case of a first order dependence on BisPin concentration.…”

Advances in the Ring Opening of Small-Ring Heterocycles with Organoboron Derivatives

“…In general, bis(pinacolato)diborane (B 2 pin 2 ) has been used in preference to other alkoxydiborons because it is stable and commercially available, and because the borylated products derived from it can be handled in air and are stable toward hydrolysis and during chromatographic purifications. 38…”