Electrophilic Triflyl-arylation and Triflyl-pyridylation by Unsymmetrical Aryl/Pyridyl-λ3-iodonium Salts: Synthesis of Aryl and Pyridyl Triflones

被引:15
作者
Das, Prajwalita [1 ]
Shibata, Norio [1 ]
机构
[1] Nagoya Inst Technol, Dept Nanopharmaceut Sci, Dept Life Sci & Appl Chem, Showa Ku, Nagoya, Aichi 4668555, Japan
关键词
ONE-POT SYNTHESIS; POSITRON-EMISSION-TOMOGRAPHY; DIARYLIODONIUM SALTS; REGIOSELECTIVE SYNTHESIS; HETEROARYL TRIFLONES; MEDICINAL CHEMISTRY; ISOXAZOLE TRIFLONES; LIQUID-CRYSTALS; VINYL TRIFLONES; EFFICIENT;
D O I
10.1021/acs.joc.7b01690
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Unsymmetrical diaryl-lambda(3)-iodonium salts containing aryl triflone (Ar-SO2CF3) were designed and synthesized. X-ray crystal structure analysis of the salt indicated a T-shaped geometry at the iodine atom. The salts were found to be powerful electrophilic reagents for triflyl-arylation of C-, N-, and O-centered nucleophiles under mild conditions. Electrophilic transfer of pyridine triflone (Py-SO2CF3) to nucleophiles was also realized by the use of corresponding triflylpyridyl-aryl-lambda(3)-iodonium salts. Selection of auxiliaries (dummy ligands) of unsymmetrical diaryl-lambda(3)-iodonium salts is crucial for this transformation.
引用
收藏
页码:11915 / 11924
页数:10
相关论文
共 72 条
[1]   Endothermic energy transfer: A mechanism for generating very efficient high-energy phosphorescent emission in organic materials [J].
Adachi, C ;
Kwong, RC ;
Djurovich, P ;
Adamovich, V ;
Baldo, MA ;
Thompson, ME ;
Forrest, SR .
APPLIED PHYSICS LETTERS, 2001, 79 (13) :2082-2084
[2]   Fluoride based electrode materials for advanced energy storage devices [J].
Amatucci, Glenn G. ;
Pereira, Nathalie .
JOURNAL OF FLUORINE CHEMISTRY, 2007, 128 (04) :243-262
[3]  
[Anonymous], ANGEW CHEM INT ED
[4]   A new class of 3′-sulfonyl BINAPHOS ligands:: Modulation of activity and selectivity in asymmetric palladium-catalysed hydrophosphorylation of styrene [J].
Barta, Katalin ;
Francio, Giancarlo ;
Leitner, Walter ;
Lloyd-Jones, Guy C. ;
Shepperson, Ian R. .
ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (13) :2013-2023
[5]   Efficient and general one-pot synthesis of diaryliodonium triflates: Optimization, scope and limitations [J].
Bielawski, Marcin ;
Zhu, Mingzhao ;
Olofsson, Berit .
ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (17-18) :2610-2618
[6]   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
[7]   One-Pot Synthesis and Applications of N-Heteroaryl Iodonium Salts [J].
Bielawski, Marcin ;
Malmgren, Joel ;
Pardo, Leticia M. ;
Wikmark, Ylva ;
Olofsson, Berit .
CHEMISTRYOPEN, 2014, 3 (01) :19-22
[8]   Addition of trifluoromethanethio- and trifluoromethaneseleno-sulfonates to olefins. Synthesis of vinyl triflones. [J].
Billard, T ;
Langlois, BR .
TETRAHEDRON, 1999, 55 (26) :8065-8074
[9]  
BOIKO VN, 1987, ZH ORG KHIM+, V23, P2586
[10]   Tetrahydropyridine-4-carboxamides as novel, potent transient receptor potential vanilloid 1 (TRPV1) antagonists [J].
Brown, Brian S. ;
Keddy, Ryan ;
Zheng, Guo Zhu ;
Schmidt, Robert G. ;
Koenig, John R. ;
McDonald, Heath A. ;
Bianchi, Bruce R. ;
Honore, Prisca ;
Jarvis, Michael F. ;
Surowy, Carol S. ;
Polakowski, James S. ;
Marsh, Kennan C. ;
Faltynek, Connie R. ;
Lee, Chih-Hung .
BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (18) :8516-8525