348613-08-1Relevant articles and documents
Directed Remote Lateral Metalation: Highly Substituted 2-Naphthols and BINOLs by In Situ Generation of a Directing Group
Patel, Jignesh J.,Laars, Marju,Gan, Wei,Board, Johnathan,Kitching, Matthew O.,Snieckus, Victor
, p. 9425 - 9429 (2018)
A general synthesis of highly substituted 2-naphthols based on a new carbanionic reaction sequence is demonstrated. The reaction exploits the dual nature of lithium bases consisting of consecutive ring opening of readily available coumarins with either LiNEt2 or LiNiPr2 into Z-cinnamamides, thus generating a directing group in situ and allowing, by conformational freedom, a lateral directed remote metalation for ring closure to give the aryl 2-naphthols in good to excellent yields. These transformations can be combined to provide a more efficient one-pot process. Mechanistic insight into the remote lateral metalation step, demonstrating the requirement of Z-cinnamamide, is described. Application of this methodology to the synthesis of highly substituted 3,3′-diaryl BINOL ligands is also reported.
A practical in situ generation of the schwartz reagent. reduction of tertiary amides to aldehydes and hydrozirconation
Zhao, Yigang,Snieckus, Victor
, p. 390 - 393 (2014/04/03)
A new, highly efficient in situ protocol (Cp2ZrCl2/LiAlH(OBu-t)3) is described for the generation of the Schwartz reagent which provides a convenient method for the amide to aldehyde reduction and the regioselective hydrozirconation-iodination of alkynes and alkenes. Highlighted are chemoselective reductions of benzamides derived by directed ortho metalation (DoM) chemistry, allowing the synthesis of valuable 1,2,3-substituted benzaldehydes. The single-step, three-component process proceeds in a very short reaction time, shows excellent functional group compatibility, and uses inexpensive and long-storage stable reducing reagents.
Metaphenylenediamines in dyeing compositions for keratinic fibers
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, (2008/06/13)
Dye compositions comprising a coupler having to the formula STR1 in which formula R1 and R2 are identical or different and represent a hydrogen atom or an alkyl radical having 1 to 2 carbon atoms and n represents a number equal to 1 or 2 and a paraphenylenediamine. This coupler is particularly suitable for use in a dyeing composition comprising paraphenylenediamines responding to the formula STR2 or the corresponding acid salts; formula in which R1, R2 and R3 are identical or different and represent a hydrogen atom, an alkyl or alkoxy radical having 1 to 2 carbon atoms, R4 and R5 are identical or different and represent a hydrogen atom, a alkyl radical, hydroxyalkyl, alkoxyalkyl in which the alkoxy group comprises 1 to 2 carbon atoms, carbamylalkyl, mesylaminoalkyl, acetylaminoalkyl, ureidoaminoalkyl, carbethoxyaminoalkyl, the alkyl groups in R4 and R5 having 1 to 3 carbon atoms, with the reservation that R1 or R3 represents hydrogen when R4 and R5 do not represent a hydrogen atom.