143192-59-0

Upstream product

• 591-50-4 iodobenzene 
• 120651-33-4 ((2‐ethynylphenyl)ethynyl)trimethylsilane 
• 137648-47-6 1-iodo-2-ethynylbenzene 
• 536-74-3 phenylacetylene 
• 21375-88-2 1-bromo-2-(phenylethenyl)benzene 
• 1066-54-2 trimethylsilylacetylene 
• 583-53-9 2,3-dibromobenzene 
• 13984-49-1 (phenylethynyl)zinc chloride 
• 583-55-1 1-Bromo-2-iodobenzene 
• 615-42-9 1,2-Diiodobenzene 
• 78389-87-4 ((trimethylsilyl)ethynyl)zinc(II) chloride 
• 38274-16-7 2-bromo-1-(trimethylsilylethynyl)benzene 

Downstream Products

• 1362738-89-3 C₃₇H₁₈BF₁₅Si 
• 1362738-77-9 C₃₇H₁₈BF₁₅Si 
• 1362738-78-0 C₃₇H₁₈BF₁₅Si 
• 399566-79-1 13-methyl-17-[3-(2-phenylethynyl-phenylethynyl)-phenylethynyl]-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol 
• 871927-95-6 3-(tert-butyl-dimethyl-silanyloxy)-13-methyl-17-[3-(2-phenylethynyl-phenylethynyl)-phenylethynyl]-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-ol 

Relevant academic research and scientific papers

Enantioselective Rh(II)-Catalyzed Desymmetric Cycloisomerization of Diynes: Constructing Furan-Fused Dihydropiperidines with an Alkyne-Substituted Aza-Quaternary Stereocenter

Described herein is an enantioselective dirhodium(II)-catalyzed cycloisomerization of diynes achieved by the strategy of desymmetrization, which not only represents a new cycloisomerization reaction of diynes but also constitutes the first Rh(II)-catalyzed asymmetric intramolecular cycloisomerization of 1,6-diynes. This protocol provides a range of valuable furan-fused dihydropiperidine derivatives with an enantiomerically enriched alkynyl-substituted aza-quaternary stereocenter in high efficiency, complete atom economy, and excellent enantioselectivity (up to 98% ee). Besides, the highly functionalized products could be easily transformed into various synthetically useful building blocks and conjugated with a series of pharmaceutical molecules. The mechanism involving a concerted [3+2] cycloaddition/[1,2]-H shift of the Rh(II) carbenoid intermediate was elucidated by DFT calculations and mechanistic studies. More importantly, the first single crystal of alkyne-dirhodium(II) was obtained to show that a η2-coordinating activation of alkynal by dirhodium(II) was involved. Weak hydrogen bondings between the carboxylate ligands and alkynal were found, which probably made the well-defined paddlewheel-like dirhodium(II) distinctive from other metal complexes in catalyzing this transformation. Furthermore, the origin of the enantioselectivity was elucidated by a Rh2(R-PTAD)4-alkyne complex and additional calculational studies.

Optically active Ag(i):: O-OPE helicates using a single homochiral sulfoxide as chiral inducer

In this work we describe the ability of a simple enantiopure sulfoxide group to promote folding of oligo ortho-phenylene ethynylenes (o-OPEs) with one helical sense. A family of foldamers with up to seven triple bonds was synthesized and fully characteriz

Synthesis of Naphthalenyl Triflates via the Cationic Annulation of Benzodiynes with Triflic Acid

A highly efficient and regioselective annulation of benzodiynes promoted by triflic acid has been developed. This protocol provides a step and atom-economic access to a series of naphthalenyl triflates. Furthermore, direct synthetic applications of this r

The Gold(I)-Mediated Domino Reaction to Fused Diphenyl Phosphoniumfluorenes: Mechanistic Consequences for Gold-Catalyzed Hydroarylations and Application in Solar Cells

A domino sequence, involving a phosphinoauration and a gold-catalyzed 6-endo-dig cyclization step, was developed. Starting from modular and simple-to-prepare phosphadiynes, π-extended phosphoniumfluorenes were synthesized. The mechanistic proposal was sup

One-pot transformation of Me3Si-/Ph2P(O)-protected ethynes to unsymmetrical arylethynes

Me3Si-/Ph2P(O)-protected ethynes were successfully transformed to unsymmetrical arylethynes via a one-pot Ph2P(O)-deprotection/ [Pd(dppf)Cl2]-catalysed coupling and one-pot Me3Si-deprotection/Sonogash

Complex Annulations through Silver Carbenoid Intermediate: An Alternative Entry to Transformations of 1,2,3-Triazoles

An alternative entry to transformations of N-sulfonyl-4-(2-(ethynyl)aryl)-1,2,3-triazoles with various generated in situ or external nucleophiles by means of silver catalysis for producing diverse functionalized isoquinolines is described. Mechanistically

Orbital Crossings Activated through Electron Injection: Opening Communication between Orthogonal Orbitals in Anionic C1-C5 Cyclizations of Enediynes

Generally, the long-range electronic communication between spatially orthogonal orbitals is inefficient and limited to field and inductive effects. In this work, we provide experimental evidence that such communication can be achieved via intramolecular electron transfer between two degenerate and mutually orthogonal frontier molecular orbitals (MOs) at the transition state. Interaction between orthogonal orbitals is amplified when the energy gap between these orbitals approaches zero, or at an “orbital crossing”. The crossing between two empty or two fully occupied MOs, which do not lead to stabilization, can be “activated” when one of the empty MOs is populated (i.e., electron injection) or one of the filled MOs is depopulated (i.e., hole injection). In reductive cycloaromatization reactions, such crossings define transition states with energies defined by both the in-plane and out-of-plane π-systems. Herein, we provide experimental evidence for the utility of this concept using orbital crossings in reductive C1-C5 cycloaromatization reactions of enediynes. Communication with remote substituents via orbital crossings greatly enhances regioselectivity of the ring closure step in comparison to the analogous radical cyclizations. We also present photophysical data pertaining to the efficiency of electron injection into the benzannelated enediynes.

Combining Traceless Directing Groups with Hybridization Control of Radical Reactivity: From Skipped Enynes to Defect-Free Hexagonal Frameworks

This work discloses the first general solution for converting oligoalkynes into polyaromatic polycyclic systems free of pentagonal defects. The efficiency and selectivity of this cascade originate from the combination of the Bu3Sn-mediated TDG

Traceless directing groups in radical cascades: From oligoalkynes to fused helicenes without tethered initiators

We report the first example of a traceless directing group in a radical cascade. The chemo- and regioselectivity of the initial attack in skipped oligoalkynes is controlled by propargyl OR moiety. Radical translocations lead to the boomerang return of the radical center to the site of initial attack where it assists the elimination of the directing functionality via β-scission in the last step of the cascade. The Bu3Sn moiety continues further via facile reactions with electrophiles as well as Stille and Suzuki cross-coupling reactions. This selective radical transformation opens a new approach for the controlled transformation of skipped oligoalkynes into polycyclic ribbons of tunable dimensions. (Chemical Equation Presented).

Triflic acid mediated cascade cyclization of aryldiynes for the synthesis of indeno[1,2-c]chromenes: Application to dye-sensitized solar cells

A new triflic acid (TfOH)-mediated cascade cyclization of ortho-anisole-substituted aryldiynes is described for the construction of indeno[1,2-c]chromenes. The cascade cyclization proceeds through an unusual TfOH-induced alkyne-alkyne cyclization followed by nucleophilic attack of the methoxy group on the benzylidene cation, which is completely different to the cyclization of ortho-aniline- or ortho-thioanisole-substituted aryldiynes. A new class of organic dyes with the indeno[1,2-c]chromene framework as both donor and π-linker were synthesized. These compounds exhibit high photovoltaic performances in dyesensitized solar cells (DSCs).