501072-30-6

Upstream product

• 591-31-1 3-methoxy-benzaldehyde 
• 693-02-7 hex-1-yne 

Downstream Products

• 1402610-89-2 benzyl hydroxy(1-(3-methoxyphenyl)hept-2-yn-1-yl)carbamate 
• 1402611-32-8 4-butyl-6-(3-methoxyphenyl)-2-phenylpyrimidine 
• 1374748-25-0 1,2,3,4,5-pentafluoro-6-{1-(3-methoxyphenyl)hepta-1,2-dien-1-yl}benzene 
• 1374748-16-9 1,2,3,4,5-pentafluoro-6-{1-(3-methoxyphenyl)hepta-1,2-dien-3-yl}benzene 
• 1374748-07-8 C₁₈H₂₇O₅P 
• 405064-68-8 1-(1-dibromomethylene-hept-2-ynyl)-3-methoxybenzene 
• 501072-33-9 1-(3-methoxyphenyl)hept-2-yn-1-one 

Relevant academic research and scientific papers

Synthesis of Vinyl-, Allyl-, and 2-Boryl Allylboronates via a Highly Selective Copper-Catalyzed Borylation of Propargylic Alcohols

An efficient methodology for the synthesis of vinyl-, allyl-, and (E)-2-boryl allylboronates from propargylic alcohols via Cu-catalyzed borylation under mild conditions is reported. In the presence of commercially available Cu(OAc)2 or Cu(acac)2 and Xantphos, the reaction affords the desired products in up to 92% yield with a broad substrate scope (43 examples). Isolation of an allenyl boronate as the reaction intermediate suggests that an insertion-elimination-type reaction, followed by borylcupration, is involved in the borylation of propargylic alcohols.

A concise access to (polyfluoroaryl)allenes by Cu-catalyzed direct coupling with propargyl phosphates

A copper-based catalyst system for the direct coupling of polyfluoroarenes with propargyl phosphates has been developed. The catalysis can provide a rapid and concise access to (polyfluoroaryl)allenes, which can be important building blocks for the synthesis of fluorinated functional materials.

Highly enantioselective addition of linear alkyl alkynes to aromatic aldehydes

An asymmetric linear alkyl alkyne addition to aromatic aldehydes catalyzed by the Ti-(R)-BINOL system is reported with high enantioselectivity and yield. Our study expands upon the synthetic scope of propargylic alcohols, which could serve as potentially useful intermediates for the synthesis of various natural products.

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.