37595-73-6Relevant articles and documents
NHC-Nickel Catalyzed C-N Bond Cleavage of Mono-protected Anilines for C-C Cross-Coupling
Xia, Ji-Bao,Zhang, Zheng-Bing
, p. 9609 - 9613 (2020)
A Ni-catalyzed aryl C-N bond cleavage of mono-protected anilines, N-arylsulfonamides, has been developed. A new N-heterocyclic carbene derived from benzoimidazole shows high reactivity for the C-N cleavage/C-C cross-coupling reaction. The ortho-directing group is not required to break the C-N bond of sulfonyl-protected anilines, which are not limited to π-extended anilines. The mechanistic studies have revealed that a sulfamidomagnesium salt is the key coupling intermediate.
Metal-free synthesis of biaryls from aryl sulfoxides and sulfonanilides via sigmatropic rearrangement
Yoshida, Akira,Okamoto, Koichi,Yanagi, Tomoyuki,Nogi, Keisuke,Yorimitsu, Hideki
, (2020/05/20)
Treatment of aryl sulfoxides and sulfonanilides with trifluoroacetic anhydride resulted in the dehydrative metal-free construction of the corresponding unsymmetrical biaryls. The reaction would proceed via (1) the activation of aryl sulfoxide with the anhydride, (2) interrupted Pummerer reaction of the resulting arylsulfonium with sulfonanilide, (3) [3,3] sigmatropic rearrangement to cleave the transient S–N bond and to form the prospective biaryl C–C bond, and (4) global aromatization. The choice of the amino protecting group is crucial, and only N-sulfonylanilines, i.e., sulfonanilides, could participate in the formation of biaryls.
Reactions of Trifluoromethanesulfonyl Azide with Aromatic Compounds
Kamigata, Nobumasa,Yamamoto, Kazutoshi,Kawakita, Osamu,Hikita, Kiyoyuki,Matsuyama, Haruo,et al.
, p. 3601 - 3602 (2007/10/02)
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