Conjugated Diyne Chemistry: Synthesis, Natural Existence and Applications

Catalytic Hydrofunctionalization Reactions of 1,3-Diynes

“…In this contribution, metal-catalyzed hydrofunctionalization reactions of conjugated 1,3-diynes have been comprehensively reviewed for this first time, thus complementing previous review articles and accounts covering the synthesis and applications of this particular class of alkynes [10][11][12][13][14][15]76]. The challenges associated with the presence of two reactive C≡C units, as the number of potential regio-and stereoisomeric products that can be formed increases, have made these substrates much less employed in hydrofunctionalization processes compared to classical monoynes.…”

“…On the other hand, although their unique structure, relative stability, and unsaturated nature have turned conjugated 1,3-diynes into useful and versatile building blocks in organic synthesis and materials science [10][11][12][13][14][15], this particular class of alkynes has been much less employed in hydrofunctionalization reactions when compared to terminal or internal monoynes. Obviously, the hydrofunctionalization of 1,3-diynes having two triple bonds and four active positions (see Figure 1) is much more challenging, since they can undergo 1,2-, 3,4-, or 1,4-monoadditions, as well as double Y-H addition processes, thus expanding the range of regioisomeric and stereoisomeric products that can be formed.…”

Hypervalent Iodine-Mediated Chemoselective Bromination of Terminal Alkynes

“…Halogenated organic compounds play an important role in organic synthesis as synthetic intermediates or key synthetic precursors due to their feasible transformation into a variety of functional compounds for material science, bioactive compounds, or industrial chemicals ( Chen et al, 2010 ; Adimurthym et al, 2013 ; Wu et al, 2017 ). For example, monohaloalkynes and α,β-dihaloalkenes have found a variety of application as dual functionalized molecules ( Brand and Waser, 2012 ; Shi and Lei, 2014 ; Wu and Jang, 2014 ; Shi, 2015 ), and α,α-dihaloketones are important building blocks in the synthesis of heterocyclic compounds, unsaturated acids and acetylenic alcohols, and cyclopropanation ( Furukawa et al, 1976 ; Kawabata et al, 1977 ; Kowalski and Fields, 1982 ; Zhdankin and Stang, 1993 ; SooáKim et al, 1995 ; Madabhushi et al, 2013 ; Sadhukhan et al, 2020 ). In addition, α,α-dihaloketones and tetrahalides have been reported to be potent antitumor, antibacterial, antifungal, antineoplastic, antiviral, and antioxidizing agents ( Butler and Walker, 1993 ; Bora et al, 2000 ; Khazaei et al, 2010 ).…”

Effective Antimalarial Activities of α-Hydroxy Diynes Isolated from Ongokea gore

“…Their study showed that the Cadiot-Chodkiewicz coupling is a method of choice for the construction of natural acetylenic compounds. Recently, Shi [26] enriched the Tykwinski study by reporting isolation of natural diynes in plant species, fungi, bacteria, marine sponges, and corals, which were uncovered in previous reviews. This paper also gave an overview of the synthetic route and applications of a 1,3-diyne structure.…”