76570-64-4

Upstream product

• 4846-21-3 O-phenylhydroxylamine 
• 98-86-2 acetophenone 
• 613-91-2 acetophenone oxime 
• 98-80-6 phenylboronic acid 
• 10341-75-0 (E)-1-phenylethanone oxime 
• 66003-76-7 Diphenyliodonium triflate 
• 1483-72-3 diphenyliodonium chloride 

Downstream Products

• 108-95-2 phenol 
• 1839-72-1 2-phenylbenzofuran 

Relevant academic research and scientific papers

An efficient synthesis of O-aryloxime ethers by copper fluorapatite catalyzed cross-coupling of aryloximes with arylboronic acids

A novel, highly efficient, and mild protocol has been developed for the synthesis of O-aryloxime ethers in good to excellent yields at ambient reaction conditions. This is the first report in which NOAr linkage was achieved with ecofriendly, recyclable, heterogeneous copper fluorapatite (CuFAP) catalyst via CO cross coupling of aryloxime with arylboronic acid in the presence of Cs2CO3as base and methanol as solvent.

Scalable, transition-metal-free direct oxime o-arylation: Rapid access to o-arylhydroxylamines and substituted benzo[b]furans

O-Aryloximes, generated from readily available and inexpensive oximes through transition-metal-free O-arylation, can either be hydrolyzed to O-arylhydroxylamines or conveniently converted to structurally diverse benzo[b]furans through an environmentally benign, one-pot [3,3]-sigmatropic rearrangement/cyclization sequence. A scalable, transition-metal-free (TM-free) direct O-arylation of ketone oximes with a wide range of diaryliodonium salts has been developed. More than two dozen O-arylated oximes have been prepared in good to excellent yields at ambient temperature and were converted to the corresponding substituted benzo[b]furans through a [3,3]-sigmatropic rearrangement/cyclization sequence. Overall, this operationally simple, environmentally benign, and protecting-group-free approach, including a one-pot variant, allows rapid and convenient synthetic access to substituted benzo[b]furans (see scheme).

O-aryloxime ethers from the copper(II)-mediated cross-coupling of oximes and phenylboronic acids

A direct approach to O-aryloxime ethers by means of the first copper-mediated cross-coupling of aromatic oximes and phenylboronic acids is reported. The O-arylation of acetophenone oximes with phenylboronic acids typically furnished O-aryloxime ethers in

Efficient synthesis of benzofurans utilizing [3,3]-sigmatropic rearrangement triggered by N-trifluoroacetylation of oxime ethers: Short synthesis of natural 2-arylbenzofurans

A new synthetic method for the preparation of benzofurans has been developed. The key step of this method is the [3,3]-sigmatropic rearrangement of N-trifluoroacetyl-ene-hydroxylamines, which was triggered by acylation of oxime ethers. TFAA has been proved to be the best reagent to induce [3,3]-sigmatropic rearrangement for the synthesis of cyclic or acyclic dihydrobenzofurans. On the other hand, the TFAT-DMAP system is found to be the most effective for constructing various benzofurans. Synthetic utility of this reaction is demonstrated by the short synthesis of natural benzofurans without protection of the hydroxy group. The synthesis of Stemofuran A was accomplished via condensation of ketones with aryloxyamine and subsequent reaction with TFAT-DMAP in a four-step synthesis with 72% overall yield. Similarly, Eupomatenoid 6 and Coumestan were synthesized through the reaction of oxime ether with TFAT-DMAP. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Highly effective synthetic methods for substituted 2-arylbenzofurans using [3,3]-sigmatropic rearrangement: Short syntheses of stemofuran A and eupomatenoid 6

Matrix presented. A new and efficient synthesis of 2-arylbenzofurans has been achieved via a route involving acylation and subsequent [3,3]-sigmatropic rearrangement of oxime ethers. Its synthetic utility is demonstrated by a short synthesis of stemofuran

Studies on the Preparation of N-Alkyl-O-phenylhydroxylamines

Several possible routes to the title compounds have been investigated.The reaction of N-hydroxycarbamates (1) with diphenyliodonium bromide gave, unexpectedly, N-hydroxy-N-phenylcarbamates (2), while N-methyl-N-hydroxycarbamates (6) gave 2-(N-methyl-N-alkoxycarbonylamino)phenols (7).Mechanistic aspects of the N-arylations and subsequent rearrangements are discussed.The desired N-alkyl-O-phenylhydroxylamines were obtained by the reduction of O-phenyloximes (15) with sodium cyanoborohydride.