1011501-99-7Relevant articles and documents
Introduction of 4-Chlorophenyl: A Protecting Group for the Hydroxy Function
Otsuka, Yuji,Yamamoto, Toshihiro,Fukase, Koichi
, p. 1510 - 1516 (2018)
4-Chlorophenyl ether was utilized as a new protecting group for the hydroxy function. This group was readily introduced to a sugar hydroxy group by using diaryliodonium triflate. Regioselective introduction of this protecting group at the vicinal cis -diol was achieved by using a copper catalyst and diaryliodonium triflate. This protecting group is stable under the Lewis acidic conditions of glycosylation, but it can be readily removed by the initial conversion into the corresponding 4-methoxyphenyl ether with use of a Pd catalyst, followed by oxidation with ammonium cerium (IV) nitrate [(NH 4) 2 Ce(NO 3) 6 ] (CAN).
Metal-free synthesis of ortho -CHO diaryl ethers by a three-component sequential coupling
Liu, Fangliang,Yang, Huameng,Hu, Xinquan,Jiang, Gaoxi
supporting information, p. 6408 - 6411 (2015/01/09)
A practical, metal-free, and highly chemoselective approach was developed for the synthesis of ortho-CHO diaryl ethers by a three-component sequential coupling of arynes, N,N-dimethylformamide (DMF), and diaryliodonium salts. Diverse functional groups including halo, nitryl, and bulky substituents and heteroaromatics are well tolerated. Mechanistically, isotopic tracer experiments reveal that the diaryliodonium salt serves as an electrophile to trap the transient intermediates generated from the [2 + 2] cyclization of an aryne and DMF.