347399-43-3

Upstream product

• 1085526-67-5 (4-tert-butylphenyl)ethynyl bromide 
• 82731-79-1 diethyl[(trimethylsilyl)acetylenyl]aluminum 
• 14630-40-1 Bis(trimethylsilyl)ethyne 
• 204578-44-9 1-(4-tert-butylphenyl)-3-trimethylsilylpropynone 
• 405064-63-3 [4,4-dibromo-3-(4-tert-butylphenyl)buten-1-ynyl]trimethylsilane 
• 35779-04-5 1-tert-butyl-4-iodobenzene 
• 4526-06-1 trimethylsilyl-1,3-butadiyne 

Downstream Products

• 347399-45-5 1-(1,3-butadiynyl)-4-tert-butylbenzene 
• 1318244-84-6 C₁₈H₂₂O 
• 1318244-85-7 C₁₈H₂₂O 
• 1318244-86-8 C₂₁H₂₆O 
• 1318244-87-9 C₁₉H₂₄O 
• 1318244-88-0 C₁₉H₂₄O 
• 1318244-89-1 C₁₇H₂₀O 

Relevant academic research and scientific papers

Highly efficient synthesis of unsymmetrical 1,3-diynes from organoalane reagents and alkynyl bromides mediated by a nickel catalyst

Highly efficient and simple cross-coupling reactions of alkynylbromides with organoalane reagents for the synthesis of unsymmetrical 1,3-diynes derivatives using Ni(OAc)2 (2-5 mol%)/(o-furyl)3P (4-10 mol%) as a catalyst are reported. Excellent yields (up to 94%) were obtained for a wide range of substrates at rt or 60 °C for 2-3 h in Et2O or toluene.

Chiral propargyl alcohols via the enantioselective addition of terminal Di- and triynes to aldehydes

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.

Synthesis of unsymmetrically substituted 1,3-butadiynes and 1,3,5-hexatriynes via alkylidene carbenoid rearrangements

Unsymmetrically substituted 1,3-butadiynes and 1,3,5-hexatriynes are synthesized in four steps from commercially available aldehydes or carboxylic acids. The key step in this process involves a Fritsch-Buttenberg-Wiechell rearrangement, in which an alkylidene carbenoid intermediate subsequently rearranges to the desired polyyne. This rearrangement proceeds under mild conditions, and it is tolerant of a range of functionalities. In general, the procedurally facile formation of the dibromoolefinic precursors, in combination with the effectiveness of the rearrangement step, makes this procedure an attractive alternative to traditional methods for di- and triyne synthesis that utilize palladium or copper catalysis.

Modification of the Fritsch-Buttenberg-Wiechell rearrangement: A facile route to unsymmetrical butadiynes

A modification of the Fritsch-Buttenberg-Wiechell rearrangement has been used to form unsymmetrically substituted 1,3-butadiynes from 1,1-dibromo-olefin precursors. The reaction proceeds via lithium-halogen exchange, followed by migration of the aryl or alkynyl moiety to provide the butadiyne framework. The facile formation of the dibromo-olefins in three steps from commercially available aryl aldehydes or carboxylic acid chlorides makes this procedure an attractive alternative to traditional methods for butadiyne synthesis.

Carbon networks based on dehydrobenzoannulenes. 4. Synthesis of "star" and "trefoil" graphdiyne substructures via sixfold cross-coupling of hexaiodobenzene

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.