1435517-99-9

Upstream product

• 18476-65-8 1-phenylpenta-4-yn-1-one 
• 624-31-7 4-tolyl iodide 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 38858-73-0 1-phenyl-1-trimethylsiloxycyclopropane 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 98-86-2 acetophenone 
• 29526-96-3 1-phenylcyclopropan-1-ol 
• 1061175-65-2 5-(p-tolyl)pent-4-ynoic acid methyl ester 
• 766-97-2 4-n-methylphenylacetylene 
• 152705-37-8 N-methoxy-N-methylpent-4-ynamide 
• 6089-09-4 4-pentynoic acid 

Downstream Products

• 1435518-42-5 3-phenyl-7-(p-tolyl)hepta-1,6-diyn-3-yl benzoate 
• 1435518-17-4 3-phenyl-7-(p-tolyl)-1-(trimethylsilyl)hepta-1,6-diyn-3-ol 

Relevant academic research and scientific papers

Alkyne Trifunctionalization via Divergent Gold Catalysis: Combining π-Acid Activation, Vinyl-Gold Addition, and Redox Catalysis

Here we report the first example of alkyne trifunctionalization through simultaneous construction of C-C, C-O, and C-N bonds via gold catalysis. With the assistance of a γ-keto directing group, sequential gold-catalyzed alkyne hydration, vinyl-gold nucleophilic addition, and gold(III) reductive elimination were achieved in one pot. Diazonium salts were identified as both electrophiles (N source) and oxidants (C source). Vinyl-gold(III) intermediates were revealed as effective nucleophiles toward diazonium, facilitating nucleophilic addition and reductive elimination with high efficiency. The rather comprehensive reaction sequence was achieved with excellent yields (up to 95%) and broad scope (>50 examples) under mild conditions (room temperature or 40 °C).

K2CO3-Mediated Cyclization and Rearrangement of γ,δ-Alkynyl Oximes to Form Pyridols

A novel K2CO3-mediated cyclization and rearrangement of γ,δ-alkynyl oximes for the synthesis of pyridols is described. The process accomplishes an efficient [1,3] rearrangement of the O-vinyl oxime intermediate which is in situ generated from the intramolecular nucleophilic addition of γ,δ-alkynyl oximes. The reaction employs readily accessible starting materials, tolerates a wide range of functional groups, and gives a variety of synthetically challenging pyridols in good yields.

Visible-Light-Induced Alkoxyl Radical Generation Enables Selective C(sp3)-C(sp3) Bond Cleavage and Functionalizations

The alkoxyl radical is an important reactive intermediate in mechanistic studies and organic synthesis; however, its current generation from alcohol oxidation heavily relies on transition metal activation under strong oxidative conditions. Here we report the first visible-light-induced alcohol oxidation to generate alkoxyl radicals by cyclic iodine(III) reagent catalysis under mild reaction conditions. The β-fragmentation of alkoxyl radicals enables selective C(sp3)-C(sp3) bond cleavage and alkynylation/alkenylation reactions with various strained cycloalkanols, and for the first time with linear alcohols.

Gold-catalyzed cycloisomerization of 1,6-diyne carbonates and esters to 2,4a-dihydro-1 H-fluorenes

A synthetic method to prepare 2,4a-dihydro-1H-fluorenes efficiently from gold(I)-catalyzed 1,2-acyloxy migration/cyclopropenation/Nazarov cyclization of 1,6-diyne carbonates and esters is described. The suggested reaction pathway provides rare examples of [2,3]-sigmatropic rearrangement in this class of compounds as well as the involvement of an in situ formed cyclopropene intermediate in gold catalysis. Experimental and ONIOM(QM:QM′) [our own n-layered integrated molecular orbital and molecular mechanics(quantum mechanics:quantum mechanics′)] computational studies based on the proposed Au carbenoid species provide insight into this unique selectivity.