347399-45-5Relevant academic research and scientific papers
Chiral propargyl alcohols via the enantioselective addition of terminal Di- and triynes to aldehydes
Graham, Erin R.,Tykwinski, Rik R.
experimental part, p. 6574 - 6583 (2011/10/05)
The enantioselective addition of di- and triynes to aldehydes is presented, including the first examples of an asymmetric triyne addition. Modification of the Carreira alkynylation protocol shows that addition of diynes and triynes to α-branched aldehydes can be complete in as little as 4 h, and these reactions give good yields and enantioselectivities (up to 98% ee) for di- and triynes tested (aryl, alkyl, and silyl). It is shown for two cases (20 and 24) that products of this asymmetric addition reaction can undergo further manipulation (desilylation and triazole formation) without affecting the enantiopurity.
Regioselective trapping of terminal di-, tri-, and tetraynes with benzyl azide
Luu, Thanh,McDonald, Robert,Tykwinski, Rik R.
, p. 6035 - 6038 (2007/10/03)
(Chemical Equation Presented) The reaction of benzyl azide with terminal di-, tri-, and tetraynes appended with a range of functional groups has been explored. Standard reaction conditions for BnN3 catalyzed by CuSO4·5H2O
Carbon networks based on dehydrobenzoannulenes. 4. Synthesis of "star" and "trefoil" graphdiyne substructures via sixfold cross-coupling of hexaiodobenzene
Wan,Haley
, p. 3893 - 3901 (2007/10/03)
The synthesis and characterization of star- and trefoil-shaped polyethynyl aromatic structures, which represent model substructures of the all-carbon network graphdiyne, are described. Assembly of these macrocycles is accomplished via 6-fold Sonogashira cross-coupling of hexaiodobenzene using Pd[P(o-Tol)3]2 and CuI as the catalytic system. The development of these modified Sonogashira conditions is detailed. This work has led to the synthesis of a new family of hexakis(phenylbutadiynyl)benzene derivatives (4a-c), the largest of which is the D3h-symmetric "trefoil" 2 and is composed of three [18]annulenes fused at a common benzene ring. Attempts at the synthesis of "wheel" 3 are also described. Compound 2 represents the largest fragment of the graphdiyne network to date. UV-vis spectroscopic studies indicate enhanced electron delocalization throughout the extended π-system.
