Iron-catalyzed cross-couplings of propargylic substrates with Grignard reagents

• Published in: Journal of organometallic chemistry Vol. 964; p. 122304
• Main Authors: Posevins, Daniels, Bäckvall, Jan-E.
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 15.04.2022
• Subjects: Cross-coupling reactions; Grignard reagents; Iron catalysis; Propargylic substrates; Iron catalysis; Propargylic substrates; Grignard reagents; Cross-coupling reactions
• ISSN: 0022-328X; 1872-8561; 1872-8561
• DOI: 10.1016/j.jorganchem.2022.122304

•Iron has emerged as a “green” and sustainable alternative to the currently widely used precious metals in catalysis.•Advances in iron-catalyzed cross-coupling of Grignard reagents with propargylic substrates are highlighted herein.•Methods for highly selective preparation of propargylic and allene products have been disclosed by several research groups, including examples that demonstrate efficient chirality transfer. One of the main challenges of modern chemical industry is the inevitable transition to greener, more sustainable manufacturing processes that utilize raw materials more effectively, minimize waste streams, and avoid the use of toxic and hazardous materials. The development of new iron-based catalytic systems can eliminate the need for the currently widely used, costly and potentially toxic heavy metal catalysts in industrially relevant chemical reactions. Prominent examples of such processes include transition metal-catalyzed cross-coupling reactions for formation of carbon-carbon (CC) bonds. This minireview outlines recent developments in the area of iron-catalyzed cross-coupling chemistry during the last couple of decades, with special emphasis on the use of propargylic substrates and Grignard reagents as coupling partners. [Display omitted]