Iron-catalyzed alkyl-alkyl suzuki-miyaura coupling

Chemoselective Suzuki-Miyaura coupling of primary and secondary alkyl halides is realized by using an iron/Xantphos catalyst. Primary and secondary alkyl bromides undergo the reaction to give the coupling products in good yields. Application to the synthesis of long-chain fatty acid derivatives is also described.     

An efficient aerobic oxidative phosphonation of a-amino CH bonds over CoNiFe hydrotalcite

An efficient and convenient heterogeneous catalytic procedure has been developed for the phosphonation of a-amino CH bonds with various dialkyl phosphites and diarylphosphine oxides using molecular oxygen as a sustainable oxidant over CoNiFe hydrotalcite. The catalytic system could tolerate various tetrahydroquinoline derivatives, and the corresponding a-amino phosphonic compounds could be obtained in good to excellent yields. Synergistic effect might exist in the oxidative phosphonation under the catalysis of CoNiFe hydrotalcite.     

Iron-catalyzed aerobic oxidative cross-coupling amidation of N,N-dimethylanilines

An efficient iron-catalyzed dehydrogenative cross-coupling amidation/imidation reaction between N,N-dimethylanilines and amides/imides is reported. The protocol uses an inexpensive and readily available Fe(NO₃)₃·9H₂O/O₂ catalytic system in the absence of additional ligands at room temperature.     

A new magnetically recoverable heterogeneous palladium catalyst for phosphonation reactions in aqueous micellar solution

A new heterogeneous palladium complex of 2‐aminothiophenol supported on nanomagnetic γ‐Fe₂O₃ was synthesized and characterized using various methods. The catalyst was used as a magnetically recoverable heterogeneous palladium catalyst for phosphonation reactions via C ? P bond formation. Using this method, a wide range of electrophilic benzenes was coupled successfully with phosphite esters (triethyl/tri‐isopropyl/triphenylphosphite and diethyl/di‐isopropyl/diphenylphosphite) in aqueous micellar solution to generate the corresponding arylphosphonates in good to high yields. The catalyst was separated using an external magnet and reused for six consecutive cycles without any significant loss of its reactivity. Copyright © 2015 John Wiley & Sons, Ltd.     

Iron-catalyzed thioesterification of methylarenes with thiols in water

An iron-catalyzed coupling reaction of methylarenes with thiols leading to thioesters has been developed. The reactions were carried out in water with tert-butyl hydroperoxide (TBHP) as the oxidant and polyoxyethanyl α-tocopheryl sebacate (PTS) as the surfactant. The reaction medium is compatible with a series of functional groups and can be reused.     

Fe(III)-catalyzed oxidative coupling of alkylnitriles with aromatic carboxylic acids: Facile access to cyanomethyl esters

The first oxidative coupling of alkylnitriles with aromatic carboxylic acids using di-tert-butyl peroxide (DTBP) as oxidant was achieved under the catalysis of ionic Fe(III) complexes bearing an imidazolinium cation. This protocol features nontoxic iron catalysis, direct α-C(sp³)–H bond oxidative esterification of alkylnitriles, non-prefunctionalized starting materials, and a broad substrate scope with outstanding steric hindrance tolerance, providing a novel, straightforward, and green approach toward cyanomethyl ester synthesis.