1224882-93-2

Upstream product

• 121-43-7 Trimethyl borate 
• 149457-45-4 4-(2-bromophenylethynyl)anisole 
• 5419-55-6 Triisopropyl borate 
• 7732-18-5 water 
• 768-60-5 4-methoxyphenylacetylen 
• 583-55-1 1-Bromo-2-iodobenzene 

Relevant academic research and scientific papers

Metal-Free Aminoiodination of Alkynes Under Visible Light Irradiation for the Construction of a Nitrogen-Containing Eight-Membered Ring System

A method for the synthesis of dihydrodibenzo[c,e]azocine derivatives via a regioselective intramolecular aminoiodination of alkynes under visible light irradiation has been developed. This protocol uses a combination of iodine and hypervalent iodine to re

Enantioselective Synthesis of 1,12-Disubstituted [4]Helicenes

A highly enantioselective synthesis of 1,12-disubstituted [4]carbohelicenes is reported. The key step for the developed synthetic route is a Au-catalyzed intramolecular alkyne hydroarylation, which is achieved with good to excellent regio- and enantioselectivity by employing TADDOL-derived (TADDOL=α,α,α,α-tetraaryl-1,3-dioxolane-4,5-dimethanol) α-cationic phosphonites as ancillary ligands. Moreover, an appropriate design of the substrate makes the assembly of [4]helicenes of different substitution patterns possible, thus demonstrating the synthetic utility of the method. The absolute stereochemistry of the newly prepared structures was determined by X-ray crystallography and characterization of their photophysical properties is also reported.

Enantioselective Synthesis of 1-Aryl Benzo[5]helicenes Using BINOL-Derived Cationic Phosphonites as Ancillary Ligands

The synthesis of unprecedented BINOL-derived cationic phosphonites is described. Through the use of these phosphanes as ancillary ligands in AuI catalysis, a highly regio- and enantioselective assembly of appropriately designed alkynes into 1-(

Controlling the Selectivity Patterns of Au-Catalyzed Cyclization-Migration Reactions

As little as 2 mol % of (XPhos)AuNTf2 catalyzes the transformation of a broad range of o-acetylene-substituted styrenes into 1,2-dihydronaphthalenes. Our data suggests that this transformation occurs via a gold-stabilized cyclopropyl carbinyl cation, which triggers either a [1,2] carboxylate shift or a less favorable [1,2] aryl shift. The relative rates of these migrations can be controlled by the identity of the ligand or by stabilizing the mesomeric cation.

Gold-catalyzed cycloisomerization of pyridine-bridged 1,8-diynes: An expedient access to luminescent cycl[3.2.2]azines

Gold-catalyzed diyne cycloisomerizations involving carbene/alkyne metathesis have been the focal point of attention for the past few years as it offers great potential to build complex polycyclic architectures. However, the design of novel cycloisomerizations has been mostly limited to 1,5/1,6-diynes and has remained very challenging to apply for higher 1,n-diynes. Herein, we disclose an unprecedented cycloisomerization of pyridine-bridged 1,8-diynes involving carbene/alkyne metathesis to access luminescent cycl[3.2.2]azines.

A new class of N-doped ionic PAHs: Via intramolecular [4+2]-cycloaddition between arylpyridines and alkynes

Reported herein, for the first time, is a copper-promoted intramolecular [4+2]-cycloaddition cascade to access ionic N-doped polycyclic aromatic hydrocarbons (PAHs) with tunable emission wavelengths. It is shown that the reaction can be made catalytic with respect to Cu(OTf)2 when an external oxidant, Selectfluor, was used.

Oxidative Intramolecular 1,2-Amino-Oxygenation of Alkynes under AuI/AuIIICatalysis: Discovery of a Pyridinium-Oxazole Dyad as an Ionic Fluorophore

Oxidative intramolecular 1,2-amino-oxygenation reactions, combining gold(I)/gold(III) catalysis, is reported. The reaction provides efficient access to a structurally unique ionic pyridinium-oxazole dyad with tunable emission wavelengths. The application of these fluorophores as potential biomarkers has been investigated.

An alternative approach to aldol reactions: Gold-catalyzed formation of boron enolates from alkynes

A new method for enolate generation via the gold-catalyzed addition of boronic acids to alkynes is reported. The formation of boron enolates from readily accessible ortho-alkynylbenzeneboronic acids proceeds rapidly with 2 mol % PPh3AuNTf2