Carbon-Phosphorus Bond Formation on Anilines Mediated by a Hypervalent Iodine Reagent

被引：21
作者：
Deruer, Elsa [1 ]
Coulibali, Siomenan [1 ]
Boukercha, Saad [1 ]
Canesi, Sylvain [1 ]
机构：
[1] Univ Quebec Montreal, Lab Methodol & Synth Prod Nat, CP 8888,Succ Ctr Ville, Montreal, PQ H3C 3P8, Canada
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 22期
基金：
加拿大自然科学与工程研究理事会; 加拿大创新基金会;
关键词：
CATALYZED DOMINO REACTION; N-ARYL; TETRAARYLPHOSPHONIUM SALTS; DEAROMATIZATION STRATEGY; ARYLATION; CONSTRUCTION; DERIVATIVES; 2-ALKYNYLANILINES; SULFONANILIDES; REARRANGEMENT;
D O I：
10.1021/acs.joc.7b01595
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Substituted anilines containing a sulfonyl group may be oxidized in situ in the presence of methanol and a hypervalent iodine reagent to form an active iminium species. Subsequent addition of phosphines or phosphites in the same pot produces meta-substituted anilines in good yields. This formal C-H bond functionalization is a direct and efficient means of selectively substituting the meta-position of anilines to produce aromatic phosphonium ions or phosphonates.
引用
收藏
页码：11884 / 11890
页数：7
相关论文
共 56 条
[1]   Asymmetric dearomative spirolactonization of naphthols using λ3-iodanes under chiral phase-transfer catalysis [J].
Antien, Kevin ;
Viault, Guillaume ;
Pouysegu, Laurent ;
Peixoto, Philippe A. ;
Quideau, Stephane .
TETRAHEDRON, 2017, 73 (26) :3684-3690
[2]   THE MICHAELIS-ARBUZOV REARRANGEMENT [J].
BHATTACHARYA, AK ;
THYAGARAJAN, G .
CHEMICAL REVIEWS, 1981, 81 (04) :415-430
[3]   Phosphorylation of C - H bonds of aromatic compounds using metals and metal complexes [J].
Budnikova, Yu H. ;
Sinyashin, O. G. .
RUSSIAN CHEMICAL REVIEWS, 2015, 84 (09) :917-951
[4]   A Highly Para-Selective Copper(II)-Catalyzed Direct Arylation of Aniline and Phenol Derivatives [J].
Ciana, Claire-Lise ;
Phipps, Robert J. ;
Brandt, Jochen R. ;
Meyer, Falco-Magnus ;
Gaunt, Matthew J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (02) :458-462
[5]   Total Synthesis of (-)-Bacchopetiolone via an Asymmetric Hydroxylative Phenol Dearomatization/[4+2]-Dimerization Cascade Promoted by a Novel Salen-Type Chiral lodane [J].
Coffinier, Romain ;
El Assal, Mourad ;
Peixoto, Philippe A. ;
Bosset, Cyril ;
Miqueu, Karinne ;
Sotiropoulos, Jean-Marc ;
Pouysegu, Laurent ;
Quideau, Stephane .
ORGANIC LETTERS, 2016, 18 (05) :1120-1123
[6]   A Stereoselective Arylative-Cyclopropanation Process [J].
Coulibali, Siomenan ;
Deruer, Elsa ;
Godin, Elizabeth ;
Canesie, Sylvain .
ORGANIC LETTERS, 2017, 19 (05) :1188-1191
[7]   Use of the Nosyl Group as a Functional Protecting Group in Applications of a Michael/Smiles Tandem Process [J].
Coulibali, Siomenan ;
Godou, Timothe ;
Canesi, Sylvain .
ORGANIC LETTERS, 2016, 18 (17) :4348-4351
[8]   Recent Advances in C-H Functionalization [J].
Davies, Huw M. L. ;
Morton, Daniel .
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (02) :343-350
[9]   Nucleophilic arylation with tetraarylphosphonium salts [J].
Deng, Zuyong ;
Lin, Jin-Hong ;
Xiao, Ji-Chang .
NATURE COMMUNICATIONS, 2016, 7
[10]   One-step formation of dihydrofuranoindoline cores promoted by a hypervalent iodine reagent [J].
Deruer, Elsa ;
Canesi, Sylvain .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (17) :3736-3741
123456