Synthesis of a Range of Iodine(III) Compounds Directly from Iodoarenes

被引:44
作者
Merritt, Eleanor A. [1 ]
Olofsson, Berit [1 ]
机构
[1] Stockholm Univ, Dept Organ Chem, Arrhenius Lab, S-10691 Stockholm, Sweden
基金
瑞典研究理事会;
关键词
Hypervalent compounds; Alkynes; Iodine; Iodonium salts; Benziodoxolones; ONE-POT SYNTHESIS; TRIFLUOROMETHANESULFONIC ACID; ALKYNYLIODONIUM SALTS; DIARYLIODONIUM SALTS; DIRECT ALKYNYLATION; FACILE SYNTHESIS; IODONIUM SALTS; HYPERVALENT; REAGENT; TRIFLUOROMETHYLATION;
D O I
10.1002/ejoc.201100360
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first direct synthesis of an alkynyl(phenyl) iodonium salt from iodobenzene and an unprotected alkyne is described. The synthesis of the corresponding alkenyl(phenyl) iodonium salt is achieved from the TMS-alkyne, simply by means of changing the solvent. The one-pot synthesis of 1-arylbenziodoxolones and other iodine(III) compounds from iodine(I) precursors is also presented.
引用
收藏
页码:3690 / 3694
页数:5
相关论文
共 49 条
[1]  
[Anonymous], 2009, Angew. Chem., Int. Ed.
[2]   SYNTHESIS OF ALKYNYL(PHENYL)IODONIUM TRIFLATES AND THEIR REACTION WITH DIETHYL 2-AMINOMALONATE [J].
BACHI, MD ;
BARNER, N ;
CRITTELL, CM ;
STANG, PJ ;
WILLIAMSON, BL .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (12) :3912-3915
[3]   ACETYLENIC AND ETHYLENIC IODONIUM SALTS AND THEIR REACTIONS WITH A CARBANION [J].
BERINGER, FM ;
GALTON, SA .
JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (06) :1930-&
[4]   Regiospecific one-pot synthesis of diaryliodonium tetrafluoroborates from arylboronic acids and aryl iodides [J].
Bielawski, Marcin ;
Aili, David ;
Olofsson, Berit .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (12) :4602-4607
[5]   High-yielding one-pot synthesis of diaryliodonium triflates from arenes and iodine or aryl iodides [J].
Bielawski, Marcin ;
Olofsson, Berit .
CHEMICAL COMMUNICATIONS, 2007, (24) :2521-2523
[6]   EFFICIENT ONE-POT SYNTHESIS OF BIS(4-TERT-BUTYLPHENYL)IODONIUM TRIFLATE [J].
Bielawski, Marcin ;
Olofsson, Berit .
ORGANIC SYNTHESES, 2009, 86 :308-314
[7]  
Brand J. P., 2009, ANGEW CHEM, V121, P9510
[8]   Benziodoxole-based hypervalent iodine reagents for atom-transfer reactions [J].
Brand, Jonathan P. ;
Gonzalez, Davinia Fernandez ;
Nicolai, Stefano ;
Waser, Jerome .
CHEMICAL COMMUNICATIONS, 2011, 47 (01) :102-115
[9]   Direct Alkynylation of Thiophenes: Cooperative Activation of TIPS-EBX with Gold and Bronsted Acids [J].
Brand, Jonathan P. ;
Waser, Jerome .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (40) :7304-7307
[10]   Direct Alkynylation of Indole and Pyrrole Heterocycles [J].
Brand, Jonathan P. ;
Charpentier, Julie ;
Waser, Jerome .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (49) :9346-9349