Recent Advances in Boron‐Substituted 1,3‐Dienes Chemistry: Synthesis and Application

Abstract

In the syntheses developed to access naturally occurring compounds, especially bioactive substances, boron-functionalized dienes (also "linchpin" reagents) are used as key reagents. Structurally unique dienes are found in nature, and play important biological and chemical roles. Recently, linchpin moieties have been proved as useful substrates for a variety of highly functionalized chemical transformations. The products of these processes are potentially of some use for the syntheses of an important class of natural products showing a wide range of biological activities. This review describes progress in the synthesis of borylsubstituted buta-1,3-dienes as well as their application in organic chemistry.

Cooperative Iodide Pd(0)‐Catalysed Coupling of Alkoxyallenes and N‐Tosylhydrazones: A Selective Synthesis of Conjugated and Skipped Dienes

“…Moreover, thanks to the very short reactiont ime, this coupling is compatible with acetylenes without producing any pyrazolef rom [3+ +2] dipolar cycloaddition (entry 21). [33] Finally the reactionw as extended to different protected alkoxyallenes (1b, c)w ithout remarkable changes with respectt ob enzyl group (entries [16][17][18][19][20]. In all cases isomer E was predominant with the E/Z ratio determined by 1 HNMR spectroscopy and gas chromotography.T races of the regioisomerd erived from the carbene a-additionw ere detected in some cases (see the Supporting Information).…”

Stereoselective Synthesis of Borylated 1,3‐Dienes by Synergistic Cu/Pd Catalysis

“…Boron‐substituted 1,3‐dienes represent an important class of compounds which serve as key building blocks in the synthesis of a wide range of bioactive natural products and organic materials . The preparation of polyene frameworks by metal‐catalyzed cross‐coupling reactions or Diels‐Alder cycloadditions which render a versatile cyclic allyl‐boron intermediate illustrate the synthetic utility of these organoboron compounds.…”

Cycloadditions of Alkenylboronic Derivatives

“…15 Several later reviews on the boron-containing 1,3dienes are also available including a review by Marciniec and co-authors published in 2017. [16][17][18] Another comprehensive review on boron-containing chiral auxiliaries was published by Pietruszka and co-authors in 2017, containing a chapter on the cycloaddition reactions. 19 In this review, the literature data from 1960s to 2019 are discussed, being categorized by the reaction type.…”