Aqueous DMSO Mediated Conversion of (2-(Arylsulfonyl)vinyl)iodonium Salts to Aldehydes and Vinyl Chlorides

被引：9

作者：

Zawia, Eman ^{[1
]}

Moran, Wesley J. ^{[1
]}

机构：

[1] Univ Huddersfield, Dept Chem, Huddersfield HD1 3DH, W Yorkshire, England

来源：

MOLECULES | 2016年 / 21卷 / 08期

关键词：

hypervalent iodine; iodonium salt; solvolysis; substitution; IODONIUM SALTS; STEREOSELECTIVE-SYNTHESIS; STEREOSPECIFIC SYNTHESIS; SUBSTITUTIONS; GENERATION; INVERSION; HALIDES; IODINE;

D O I：

10.3390/molecules21081073

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Vinyl(aryl)iodonium salts are useful compounds in organic synthesis but they are under-utilized and their chemistry is under-developed. Herein is described the solvolysis of some vinyl(phenyl) iodonium salts, bearing an arylsulfonyl group, in aqueous DMSO leading to aldehyde formation. This unusual process is selective and operates under ambient conditions. Furthermore, the addition of aqueous HCl and DMSO to these vinyl(aryl)iodonium salts allows their facile conversion to vinyl chlorides.

引用

页数：11

共 24 条

[1] Synthesis and Reactivity of Aryl(alkynyl)iodonium Salts
Dixon, Luke I.
Carroll, Michael A.
Gregson, Thomas J.
Ellames, George J.
Harrington, Ross W.
Clegg, William
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (12) : 2334 - 2345
[2] Stereochemical inversion in the vinylic substitution of boronic esters to give iodonium salts: Participation of the internal oxy group
Fujita, M
Lee, HJ
Okuyama, T
[J]. ORGANIC LETTERS, 2006, 8 (07) : 1399 - 1401
[3] Stereo- and regio-selective addition of iodotoluene difluoride to alk-1-ynes. Selective synthesis of 2-fluoro-1-iodoalk-1-enes
Hara, S
Yoshida, M
Fukuhara, T
Yoneda, N
[J]. CHEMICAL COMMUNICATIONS, 1998, (09) : 965 - 966
[4] HINKLE RJ, 1994, SYNTHESIS-STUTTGART, P313
[5] Stereospecific synthesis of (E)-alkenyl(phenyl)iodonium tetrafluoroborates via zirconium-iodane exchange
Huang, X
Xu, XH
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (20): : 3321 - 3322
[6] Stereoselective Synthesis and X-ray Structures of Alkenyliodonium Salts with a Pyridine N-Oxide Moiety
Justik, Michael W.
Kristufek, Samantha L.
Protasiewicz, John D.
Deligonul, Nihal
[J]. SYNTHESIS-STUTTGART, 2010, (14): : 2345 - 2347
[7] New one-pot method for the stereoselective synthesis of (E)-[beta(trifluoromethylsulfonyloxy)-alkenyl](aryl) iodonium triflates.
Kasumov, TM
Pirguliyev, NS
Brel, VK
Grishin, YK
Zefirov, NS
Stang, PJ
[J]. TETRAHEDRON, 1997, 53 (38) : 13139 - 13148
[8] Vinyl carbocations: Solution studies of alkenyl(aryl)iodonium triflate fragmentations
McNeil, AJ
Hinkle, RJ
Rouse, EA
Thomas, QA
Thomas, DB
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (16) : 5556 - 5565
[9] MERRITT EA, 2009, ANGEW CHEM INT EDIT, V48, P2
[10] NUCLEOPHILIC VINYLIC SUBSTITUTIONS OF (Z)-(BETA-(PHENYLSULFONYL)ALKENYL)IODONIUM TETRAFLUOROBORATES WITH TETRABUTYLAMMONIUM HALIDES - RETENTION OF CONFIGURATION
OCHIAI, M
OSHIMA, K
MASAKI, Y
[J]. TETRAHEDRON LETTERS, 1991, 32 (52) : 7711 - 7714

← 1 2 3 →