Benziodoxole-based hypervalent iodine reagents for atom-transfer reactions

被引:269
作者
Brand, Jonathan P. [1 ]
Gonzalez, Davinia Fernandez [1 ]
Nicolai, Stefano [1 ]
Waser, Jerome [1 ]
机构
[1] EPFL SB ISIC LCSO, Ecole Polytech Fed Lausanne, BCH 4306, Lab Catalysis & Organ Synth, CH-1015 Lausanne, Switzerland
基金
瑞士国家科学基金会;
关键词
HYDROXYLATIVE PHENOL DEAROMATIZATION; MILD ELECTROPHILIC TRIFLUOROMETHYLATION; GACL3-CATALYZED ORTHO-ETHYNYLATION; CATALYZED DIRECT ALKYNYLATION; IODOXYBENZOIC ACID IBX; ORGANIC-SYNTHESIS; POLYVALENT IODINE; SYNTHETIC UTILITY; OXIDATIVE DEAROMATIZATION; TERT-BUTYLPEROXYIODANES;
D O I
10.1039/c0cc02265a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In the last decades, hypervalent iodine reagents have raised from chemical curiosities to mainstream reagents in organic synthesis. The use of benziodoxole-derived reagents has been especially successful in oxidation methods, whereas non-cyclic iodinanes have been used both for oxidation and atom-transfer reactions. On the other hand, the exceptional properties of benziodoxole reagents for atom-transfer reactions have only started to attract the attention of the synthetic community more recently. In this review, progress in the use of these compounds for C-X and C-C bond formations will be presented. In particular, recent breakthroughs in trifluoromethylation and alkynylation reactions have been realized since 2006 based on benziodoxole-derived reagents and these results are the main focus of this article.
引用
收藏
页码:102 / 115
页数:14
相关论文
共 132 条
[1]   Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].
Alberico, Dino ;
Scott, Mark E. ;
Lautens, Mark .
CHEMICAL REVIEWS, 2007, 107 (01) :174-238
[2]   Palladium-catalyzed ring-forming aminoacetoxylation of alkenes [J].
Alexanian, EJ ;
Lee, C ;
Sorensen, EJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (21) :7690-7691
[3]   The Productive Merger of Iodonium Salts and Organocatalysis: A Non-photolytic Approach to the Enantioselective α-Trifluoromethylation of Aldehydes [J].
Allen, Anna E. ;
MacMillan, David W. C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (14) :4986-+
[4]   GaCl3-catalyzed ortho-ethynylation reaction of N-benzylanilines [J].
Amemiya, R ;
Fujii, A ;
Yamaguchi, M .
TETRAHEDRON LETTERS, 2004, 45 (22) :4333-4335
[5]   SYNTHESIS AND REACTION OF SUBSTITUTED ARYLALKOXYIODINANES - FORMATION OF STABLE BROMOARYLALKOXY AND ARYLDIALKOXY HETEROCYCLIC-DERIVATIVES OF TRICOORDINATE ORGANOIODINE(III) [J].
AMEY, RL ;
MARTIN, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (11) :1779-1784
[6]   Electrophilic Trifluoromethylation of Primary Phosphines: Synthesis of a P-Bis(trifluoromethyl) Derivative of BINAP [J].
Armanino, Nicolas ;
Koller, Raffael ;
Togni, Antonio .
ORGANOMETALLICS, 2010, 29 (07) :1771-1777
[7]   SYNTHESIS OF HIGHLY FUNCTIONALIZED BETA-LACTAMS - ALKYNYLATION OF 2-OXOAZETIDIN-1-YL MALONATES [J].
BACHI, MD ;
BARNER, N ;
STANG, PJ ;
WILLIAMSON, BL .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (27) :7923-7924
[8]   Recent advances in the synthesis of (hetero)aryl-substituted heteroarenes via transition metal-catalysed direct (hetero)arylation of heteroarene C-H bonds with aryl halides or pseudohalides, diaryliodonium salts, and potassium aryltrifluoroborates [J].
Bellina, Fabio ;
Rossi, Renzo .
TETRAHEDRON, 2009, 65 (50) :10269-10310
[9]   DIARYLIODONIUM SALTS .13. SALTS IN WHICH THE CATIONS BEAR CARBOXYL, HYDROXYL, ALKOXYL OR AMINO GROUPS [J].
BERINGER, FM ;
LILLIEN, I .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (03) :725-731
[10]   REARRANGEMENT + CLEAVAGE OF 2-ARYLIODONIOBENZOATES - TRAPPING AGENTS FOR BENZYNE [J].
BERINGER, FM ;
HUANG, SJ .
JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (02) :445-&