Continuous flow as an enabling technology: a fast and versatile entry to functionalized glyoxal derivatives. Issue 11 (1st March 2021)

• Record Type: Journal Article
• Authors: Lima, Fabio; Meisenbach, Mark; Schenkel, Berthold; Sedelmeier, Joerg
• Is Part Of: Organic & biomolecular chemistry. Volume 19:Issue 11(2021)
• Page Start: 2420
• Page End: 2424
• Publication Date: 2021-03-01
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d1ob00288k
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Continuous Flow methods to access glyoxal derivatives, which serve as valuable precursors for heterocyclic chemistry. Abstract : We herein report two complementary strategies employing organolithium chemistry for the synthesis of glyoxal derivatives. Micro-mixer technology allows for the generation of unstable organometallic intermediates and their instantaneous in-line quenching with esters as electrophiles. Selective mono-addition was observed via putative stabilized tetrahedral intermediates. Advantages offered by flow chemistry technologies facilitate direct and efficient access to masked 1, 2-dicarbonyl compounds while mitigating undesired by-product formation. These two approaches enable the production of advanced and valuable synthetic building blocks for heterocyclic chemistry with throughputs of grams per minute.