Alkynylboron compounds in organic synthesis

Alkynylboron compounds, consisting of alkynyl and boron moieties, can be categorized according to the substituents on the boron atom, such as alkynylboranes, -boronates, and -borates. In this review, the synthesis and reactions of alkynylboron compounds are systematically introduced. Alkynylpinacolatoboranes and alkynyltrifluoroborates are the most widely utilized classes in organic reactions, owing to their stability and ease of handling. Other alkynylboron compounds have also been developed as convenient substrates for various organic reactions. Thanks to the dedication of many chemists in this field, great advances of facile synthesis and wide utilization of alkynylboron compounds have been made with these versatile building blocks for diverse structures in organic synthesis.

Graphical abstractA series of alkynylboron compounds, consisting of alkynyl and boron moieties, have been synthesized that have helped to elucidate the various organic reactions. The understanding of a historical overview of alkynylboron compounds which contributed to the unique reactions, affording the versatile building blocks for diverse structures.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Alkynylboron compounds as useful substrates in organic synthesis. ► Cycloaddition reactions and their mechanistic insights. ► Regio- and stereoselective synthesis of multi-substituted olefins.