Transition-Metal-Free N-Arylation of N-Methoxysulfonamides and N,O-Protected Hydroxylamines with Trimethoxyphenyliodonium (III) Acetates

被引:10
|
作者
Kikushima, Kotaro [1 ]
Morita, Aki [1 ]
Elboray, Elghareeb E. [1 ,2 ]
Bae, Taeho [1 ]
Miyamoto, Naoki [1 ]
Kita, Yasuyuki [3 ]
Dohi, Toshifumi [1 ,3 ]
机构
[1] Ritsumeikan Univ, Coll Pharmaceut Sci, 1-1-1 Nojihigashi, Kusatsu, Shiga 5258577, Japan
[2] South Valley Univ, Fac Sci, Dept Chem, Qena 83523, Egypt
[3] Ritsumeikan Univ, Res Org Sci & Technol, 1-1-1 Nojihigashi, Kusatsu, Shiga 5258577, Japan
来源
SYNTHESIS-STUTTGART | 2022年 / 54卷 / 23期
关键词
N-arylation; iodonium salt; sulfonamide; hydroxylamine; sulfa drug; NUCLEOPHILIC AROMATIC-SUBSTITUTION; ONE-POT SYNTHESIS; C-H AMINATION; DIARYLIODONIUM SALTS; HYPERVALENT IODINE; SELECTIVE ARYLATION; CASCADE ANNULATION; EFFICIENT METHOD; NITROARENES; AMINES;
D O I
10.1055/a-1922-8846
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Trimethoxyphenyliodonium(III) acetate [TMP-iodonium(III) acetate] functions as an efficient arylation reagent for N,O-protected hydroxylamines, generating aniline derivatives in the absence of transition metal catalysts. Various N-methoxysulfonamides participated in the amination reaction to produce the corresponding N-methoxysulfonylanilines. This amination reaction was compatible with several protecting groups, including Troc (2,2,2-trichloroethoxycarbonyl), Cbz (benzyloxycarbonyl), Boc (tert-butoxycarbonyl), benzyl, acetyl, and silyl groups. This method uses TMP-iodonium(III) acetate and efficiently synthesizes various aniline derivatives that are versatile synthetic intermediates for functional organic molecules.
引用
收藏
页码:5192 / 5202
页数:11
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