66154-03-8

Upstream product

• 4409-84-1 2-deuteriotoluene 
• 857001-55-9 1-bromomethyl-2-deuterio-benzene 
• 50535-19-8 2-deuterobenzylidenedichloride 
• 91996-53-1 l'alcool benzylique o-deuterie 
• 95-46-5 2-methylphenyl bromide 
• 932-31-0 ortho-tolylmagnesium bromide 
• 100-52-7 benzaldehyde 
• 35822-58-3 2-bromobenzaldehyde diethyl acetal 
• 6630-33-7 ortho-bromobenzaldehyde 
• 18982-54-2 o-bromobenzyl alcohol 
• 34824-58-3 2-(2-bromophenyl)-1,3-dioxolan 
• 446-52-6 2-Fluorobenzaldehyde 
• 195004-63-8 N-tert-butyl-1-(2-fluorophenyl)methanimine 

Downstream Products

• 944275-84-7 C₁₀H₈⁽²⁾HN₃O₂ 
• 1227857-84-2 (2-bromophenyl)[(2-d₁)phenyl]methanol 
• 1380243-55-9 C₂₁H₁₃⁽²⁾HO 
• 4551-39-7 2-deuteriobenzoic acid 

Relevant academic research and scientific papers

Chromium-Catalyzed Selective Cross-Electrophile Coupling between Unactivated C(aryl)-F and C(aryl)-O Bonds

Chemically inert C(aryl)-F bonds have rarely been used to couple with other unactivated bonds, and this remains a challenge because of the difficulty of the successive cleavage of two unactivated bonds by metal catalysis. We report here the chromium-catalyzed cleavage of chemically inert C(aryl)-F bonds for coupling with unactivated C(aryl)-O bonds, allowing cross-electrophile coupling between unreactive aryl fluorides and aryl esters to be achieved in high regio- and chemoselectivity. The reactive Cr, which was formed in situ by reducing CrCl2, enables cleavage of the o-C(aryl)-F bonds to afford monovalent and quartet cyclochromate; subsequent bipyridyl-enabled insertion into the ester C(aryl)-O bond followed by reductive elimination allowed the orthogonal coupling of these two different and unactivated bonds. Mechanistic studies indicate that the bipyridyl ligand greatly enhances the reactivity of Cr in the cleavage of C(aryl)-O bonds, and the second oxidative addition may occur sluggishly compared with the reductive elimination in the catalytic cycle.

Palladium-Catalyzed Dehydrogenative Fluoroalkoxylation of Benzaldehydes

A direct and efficient palladium-catalyzed oxidative dehydrogenative fluoroalkoxylation of benzaldehydes is reported here for the first time. The method features mild reaction conditions, good tolerance of functional groups, and a broad substrate scope. The protocol employs the transient directing group strategy, thereby avoiding the additional installation and removal of directing groups, endowing the method with great advantages of atom and step economy. The approach should find broad applications in drug synthesis and discovery processes.

Selective Cross-Dehydrogenative C(sp3)-H Arylation with Arenes

Selective C(sp3)-C(sp2) bond construction is of central interest in chemical synthesis. Despite the success of classic cross-coupling reactions, the cross-dehydrogenative coupling between inert C(sp3)-H and C(sp2)-H bonds represents an attractive alternative toward new C(sp3)-C(sp2) bonds. Herein, we establish a selective inter-and intramolecular C(sp3)-H arylation of alcohols with nondirected arenes that thereby provides a general pathway to access a wide range of β-arylated alcohols, including tetrahydronaphthalen-2-ols and benzopyran-3-ols, with high to excellent chemo-and regioselectivity.

A Bu4N[Fe(CO)3(NO)]-Catalyzed Hemetsberger–Knittel Indole Synthesis

The nucleophilic Fe complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]) catalyzes the direct intramolecular amination of aryl vinyl azides to give the corresponding indole derivatives in good to excellent yields.

Generation of Donor/Donor Copper Carbenes through Copper-Catalyzed Diyne Cyclization: Enantioselective and Divergent Synthesis of Chiral Polycyclic Pyrroles

The generation of metal carbenes from readily available alkynes represents a significant advance in metal carbene chemistry. However, most of these transformations are based on the use of noble-metal catalysts and successful examples of such an asymmetric version are still very scarce. Here a copper-catalyzed enantioselective cascade cyclization of N-propargyl ynamides is reported, enabling the practical and atom-economical construction of diverse chiral polycyclic pyrroles in generally good to excellent yields with wide substrate scope and excellent enantioselectivities (up to 97:3 e.r.). Importantly, this protocol represents the first copper-catalyzed asymmetric diyne cyclization. Moreover, mechanistic studies revealed that the generation of donor/donor copper carbenes is presumably involved in this 1,5-diyne cyclization, which is distinctively different from the related gold catalysis, and thus it constitutes a novel way for the generation of donor/donor metal carbenes.

Rh-Catalyzed Annulation of ortho-C?H Bonds of 2-Arylimidazoles with 1,4,2-Dioxazol-5-ones toward 5-Arylimidazo[1,2-c]quinazolines

A Rh-catalyzed unique and direct approach for constructing a series of 5-arylimidazo[1,2-c]quinazolines in moderate to excellent yields from simple and readily available 2-arylimidazoles and 3-phenyl-1,4,2-dioxazol-5-ones was described. This procedure pro

Weakly Coordinating, Ketone-Directed Cp?Co(III)-Catalyzed C-H Allylation on Arenes and Indoles

Weakly coordinating, ketone-directed, regioselective monoallylation of arenes and indoles is reported using a stable and cost-effective high-valent cobalt(III)-catalyst to access several important molecular building blocks. The allylation proceeds smoothl

Nitrate-promoted Selective C-H Fluorination of Benzamides and Benzeneacetamides

A versatile and site-selective nitrate-promoted C-H bond fluorination using various weak coordinating amides as intrinsic directing groups was developed. Diverse tertiary and secondary amides underwent selective aromatic C-H bond fluorination, which featu

Cp?CoIII-Catalyzed syn-Selective C-H Hydroarylation of Alkynes Using Benzamides: An Approach Toward Highly Conjugated Organic Frameworks

Hydroarylation of internal alkynes by cost-effective CoIII-catalysis, directed by N-tert-butyl amides, is achieved to avail mono- or dihydroarylated amide products selectively in an atom and step economic way. Several important functional groups were tolerated under the reaction conditions, and syn-hydroarylation products were exclusively isolated. Notably, a 4-fold C-H hydroarylation provided a highly conjugated organic framework in one step. Kinetic study with extensive deuterium labeling experiments were performed to support the proposed mechanism.

Rh(III)-Catalyzed bilateral cyclization of aldehydes with nitrosos toward unsymmetrical acridines proceeding with C-H functionalization enabled by a transient directing group

A Rh(iii)-catalyzed bilateral cyclization was developed for the efficient construction of acridines proceeding with C-H functionalization whereby in situ formation and removal of an imino transient directing group in the presence of catalytic amount of BnNH2 are achieved. In this transformation, a sequential Rh(iii)-catalyzed C-H amination, cyclization, and aromatization process was involved.