Highly Selective Catalytic Synthesis of (E,E)-1,4-Diiodobuta-1,3-diene via Atom-Efficient Addition of Acetylene and Iodine: A Versatile (E,E)-1,3-Diene Building Block in Cross-Coupling Reactions

Abstract

The first practical procedure is reported for the synthesis of (E,E)-1,4-diiodobuta-1,3-diene from very simple starting materials (acetylene and I 2 ). A pure crystalline product was obtained in a green chemical procedure utilizing the key advantages of highly selective Pt-catalyzed transformation and 100% atom efficiency of the addition reaction. The Pt catalyst was recovered and re-used in the reaction without a noticeable loss of activity.

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

“…In the same way, the stereo‐defined construction of functionalised conjugated dienes represents a major goal in organic synthesis, and many efforts have been devoted in the past decades exploiting metal‐catalysed couplings of alkynes or allenes and suitable alkenes or 1,4 elimination processes . Nevertheless, great attention is still paid to their preparation –. Domino allylic alkylation/4π‐electrocyclic ring opening, ring‐closing metathesis, allene–Claisen rearrangement and Pd‐catalysed coupling of allenes and boronic derivatives were reported.…”

Evidence for the “cocktail” nature of platinum-catalyzed alkyne and alkene hydrosilylation reactions

“…Atom-economic catalytic addition reactions of various heteroatom-hydrogen (E-H) bonds to unsaturated substrates have enriched the field of organic synthesis by introducing a number of powerful synthetic approaches. 1 Using transition metal catalysis, various highly efficient catalytic systems leading to stereo-and regioselective carbon-heteroatom bond construction have been developed for C-Si, 2 C-S, [3][4][5][6] C-P, [7][8][9] C-Se, 4,10 C-N, 11,12 C-O, 11,13 C-I, 14,15 and other C-E bonds formation.…”

Catalytic C–C and C–Heteroatom Bond Formation Reactions: In Situ Generated or Preformed Catalysts? Complicated Mechanistic Picture Behind Well-Known Experimental Procedures

“…Addition reactions are atom-economic and do not produce waste; thus, they comply with green chemistry approaches by intrinsic design. These reactions were successfully used for the construction of C–N, C–O, C–P, C–S, C–Se, and C–I bonds (Scheme B). , …”