60907-57-5

Upstream product

• 110-00-9 furan 
• 3433-80-5 1-Bromo-2-bromomethyl-benzene 
• 2786-02-9 2-lithiofuran 
• 13331-23-2 fur-2-ylboronic acid 
• 143238-84-0 (2-bromophenyl)methyl methanesulfonate 
• 18982-54-2 o-bromobenzyl alcohol 

Downstream Products

• 114325-51-8 1-(2-Bromo-benzyl)-11-oxa-tricyclo[6.2.1.0^2,7]undeca-2,4,6,9-tetraene 
• 238-84-6 benzo[a]fluorene 
• 1638147-33-7 1-(2-(furan-2-ylmethyl)phenyl)-3-phenylprop-2-yn-1-yl methyl carbonate 
• 114325-53-0 C₂₁H₁₆O 
• 123100-39-0 C₂₁H₁₅BrO 
• 60993-78-4 3-(2-bromo-benzyl)-pyridazine 

Relevant academic research and scientific papers

Synthetic method of diarylmethanes

The invention discloses a synthetic method of diarylmethanes. The method is characterized in that benzyl pseudohalide and aromatic boric acid are reacted in an organic solvent under alkaline condition. The method employs easily available raw materials, conversion is realized under effect of no transition metal catalysis, water-free and oxygen-free are not required, Lewis acid catalysis is not required, the method has wide substrate universality, and various substituted diarylmethanes can be synthesized by the method.

Coupling N-H Deprotonation, C-H Activation, and Oxidation: Metal-Free C(sp3)-H Aminations with Unprotected Anilines

An intramolecular oxidative C(sp3)-H amination from unprotected anilines and C(sp3)-H bonds readily occurs under mild conditions using t-BuOK, molecular oxygen and N,N-dimethylformamide (DMF). Success of this process, which requires mildly acidic N-H bonds and an activated C(sp3)-H bond (BDE 85 kcal/mol), stems from synergy between basic, radical, and oxidizing species working together to promote a coordinated sequence of deprotonation: H atom transfer and oxidation that forges a new C-N bond. This process is applicable for the synthesis of a wide variety of N-heterocycles, ranging from small molecules to extended aromatics without the need for transition metals or strong oxidants. Computational results reveal the mechanistic details and energy landscape for the sequence of individual steps that comprise this reaction cascade. The importance of base in this process stems from the much greater acidity of transition state and product for the 2c,3e C-N bond formation relative to the reactant. In this scenario, selective deprotonation provides the driving force for the process.

Coupling of arylboronic acids with benzyl halides or mesylates without adding transition metal catalysts

We report herein a transition-metal-free coupling reaction of arylboronic acids with benzyl halides and mesylates for the construction of C(sp2)[sbnd]C(sp3) bonds. A unique feature of this coupling reaction is the formation regioisomers in some cases. Mechanistic studies suggest that this reaction may proceed via an unprecedented Friedel–Crafts-type reaction pathway under base conditions with the assistance of boronic acid moiety.

Gold-Catalyzed Cyclization of Furan-Ynes bearing a Propargyl Carbonate Group: Intramolecular Diels–Alder Reaction with In Situ Generated Allenes

Gold-catalyzed cyclization of various furan-ynes with a propargyl carbonate or ester moiety results in the formation of a series of polycyclic aromatic ring systems. The reactions can be rationalized through a tandem gold-catalyzed 3,3-rearrangement of the propargyl carboxylate moiety in furan-yne substrates to form an allenic intermediate, which is followed by an intramolecular Diels–Alder reaction of furan and subsequent ring-opening of the oxa-bridged cycloadduct. It was found that the steric and electronic properties of phosphine ligands on the gold catalyst had a significant impact on the reaction outcome. In the case of 1,5-furan-yne, the cleavage of the oxa-bridge in the cycloadduct with concomitant 1,2-migration of the R1group occurs to furnish anthracen-1(2H)-ones bearing a quaternary carbon center. For 1,4-furan-yne, a facile aromatization of the cycloadduct takes place to give 9-oxygenated anthracene derivatives.

Organocatalytic Nonclassical Trienamine Activation in the Remote Alkylation of Furan Derivatives

A new approach for the stereoselective remote alkylation of furan derivatives is reported. The reaction of 5-alkylfurfurals with nitroolefins as electrophilic counterparts occurs at their exocyclic ε-position and proceeds through the intermediacy of a non

Catalytic chemical amide synthesis at room temperature: One more step toward peptide synthesis

An efficient method has been developed for direct amide bond synthesis between carboxylic acids and amines via (2-(thiophen-2-ylmethyl)phenyl)boronic acid as a highly active bench-stable catalyst. This catalyst was found to be very effective at room temperature for a large range of substrates with slightly higher temperatures required for challenging ones. This methodology can be applied to aliphatic, α-hydroxyl, aromatic, and heteroaromatic acids as well as primary, secondary, heterocyclic, and even functionalized amines. Notably, N-Boc-protected amino acids were successfully coupled in good yields with very little racemization. An example of catalytic dipeptide synthesis is reported.

Scope of Tandem Cycloaddition/Radical Cyclization Methodology

Tandem cycloaddition/radical cyclization is an effective strategy for the rapid assembly of a wide variety of ring systems.To set up the reagents for this sequence, it is necessary to include a potential radical site in one of the two cycloaddition partners, located at an appropriate distance from a new double bond that will be formed in the cycloaddition step.Examples in which the cycloaddition step is or and in which the radical cyclization creates 5-, 6-, or 7-membered rings are described.Examples of the tandem methodology carried out in a completely intramolecular mode are also described.

Tandem Cycloaddition/Radical Cyclization, a Widely Applicable Strategy for the Rapid Assembly of Polycyclic Systems

By treating a diene (or 1,3-dipole) that contains an appropriately located potential radical site successively with a dienophile (or dipolarophile) and a radical source one can construct a variety of polycyclic systems in two steps.