349537-53-7

Upstream product

• 7147-44-6 1-(2-chlorophenyl)ethanone oxime 
• 108-24-7 acetic anhydride 
• 2142-68-9 1-(2-chlorophenyl)ethanone 
• 95-57-8 2-monochlorophenol 
• 5202-78-8 acetylaminoethylene 
• 66107-36-6 2-chlorophenyl triflate 

Downstream Products

• 1620165-40-3 (Z)-N-(1-(2-chlorophenyl)-4-(triisopropylsilyl)but-1-en-3-yn-1-yl)acetamide 
• 103261-03-6 2-(2-chlorophenyl)-2-oxoethyl acetate 

Relevant academic research and scientific papers

Direct Enamido C(sp2)?H Diphosphorylation Enabled by a PCET-Triggered Double Radical Relay: Access to gem-Bisphosphonates

Herein we report a novel and straightforward protocol for the construction of valuable gem-BPs by means of proton-coupled electron-transfer (PCET)-triggered enamido C(sp2)?H diphosphorylation. This reaction represents a rare example of realizing the challenging double C?P bond formation at a single carbon atom, thus providing facile access to a broad variety of structurally diverse bisphosphonates from simple enamides under silver-mediated conditions. Initial mechanistic studies demonstrated that the diphosphorylation involves two rounds of PCET-initiated radical relay process.

Merging alkenyl C-H activation with the ring-opening of 1,2-oxazetidines: Ruthenium-catalyzed aminomethylation of enamides

1,2-Oxazetidines have been utilized as formaldimine precursors for the direct aminomethylation of enamides under a Ru(ii) species. By merging alkenyl C-H activation with ring-opening of 1,2-oxazetidines, this efficient protocol provides a facile and novel

The ruthenium-catalyzed C-H functionalization of enamides with isocyanates: Easy entry to pyrimidin-4-ones

Ruthenium-catalyzed heteroannulation between enamides and isocyanates has been realized as a complementary approach to conventional strategies for the synthesis of pyrimidin-4-ones. High step-A nd atom-economy was achieved for the rapid construction of such privileged scaffolds, which are found in a multitude of pharmaceutical compounds. The generality and practicability of this transformation were reflected by the broad scope of substrates with diverse functional groups, large-scale synthesis, and late-stage diversification.

Iron-Catalyzed Radical Cycloaddition of 2H-Azirines and Enamides for the Synthesis of Pyrroles

A novel and efficient Fe-catalyzed radical cycloaddition of 2H-azirines and enamides for the synthesis of substituted pyrroles has been developed. The radical cycloaddition reaction proceeded through a conceptually new Fe(II)-catalyzed homolytic cleavage of C-N bond of 2H-azirines sequential radical cyclization with enamides. The reaction used readily available starting materials, tolerated various functional groups, and afforded valuable triaryl-substituted pyrroles in good to high yields under mild reaction conditions.

Rhodium(iii)-catalyzed olefinic C-H alkynylation of enamides at room temperature

Rh(iii)-catalyzed C-H olefinic alkynylation of enamides for the stereospecific construction of synthetically useful Z-type enynamides is reported. This protocol displays good functionality tolerance and operational simplicity thus providing an alternative synthetic opportunity for the ease of access to specific 1,3-enyne derivatives.

Direct oxidative coupling of enamides and 1,3-dicarbonyl compounds: A facile and versatile approach to dihydrofurans, furans, pyrroles, and dicarbonyl enamides

An efficient manganese(III)-mediated oxidative coupling reaction between α-aryl enamides and 1,3-dicarbonyl compounds has been developed. A series of dihydrofurans and dicarbonyl enamides were synthesized in moderate to good yields. Moreover, these dihydrofurans could be readily transformed into the corresponding furans and pyrroles via the Paal-Knorr reaction.

Synthesis of enamides via Rh/C-catalyzed direct hydroacylation of ketoximes

(Chemical Equation Presented) Enamides were efficiently prepared via a novel Rh/C-catalyzed direct hydroacylation of ketoximes. Up to 88% isolated yield of enamides were obtained with this method. Subsequent asymmetric hydrogenation of the enamides with Rh/DuanPhos complex gave the corresponding chiral amine in excellent enantioselectivities (up to 99.7% ee).

A complementary method to obtain N-acyl enamides using the Heck reaction: Extending the substrate scope for asymmetric hydrogenation

A series of N-acyl enamides were prepared using the Heck reaction. Asymmetric hydrogenation provided protected amines in up to 99% ee. A method to prepare N-acyl enamides is reported that is complementary to the existing protocols. Heck reaction of a vari