Abstract
The chemistry of hypervalent iodine compounds has been experiencing considerable attention of organic chemists during the past few years. Hypervalent iodine reagents have found ubiquitous applications in organic synthesis because of their mild and highly chemoselective oxidizing properties, easy commercial availability, and environmental benign character. Along with oxidation of alcohol, they have also shown to be useful in number of organic transformations which include oxidative functionalization of carbonyl compounds, catalytic imidations, cyclization, oxidative coupling of phenols, amines and related compounds. Among various hypervalent iodine reagents, iodine-V compounds (λ5-iodanes) have attracted much attention in recent years. This review narrates the particular advances in iodine (V) reagents with special emphasis on the use of DMP in organic transformations.
Keywords: Aromatization, cyclization, DMP, hypervalent iodine, IBX, oxidation.
Graphical Abstract
[http://dx.doi.org/10.1021/cr010003] [PMID: 12105935]
[http://dx.doi.org/10.1016/S0040-4020(96)00970-2]
[http://dx.doi.org/10.1016/S0040-4020(98)00410-4]
[http://dx.doi.org/10.1070/RC2000v069n02ABEH000557]
[http://dx.doi.org/10.1039/a909041j]
[http://dx.doi.org/10.1021/acs.chemrev.5b00547] [PMID: 26861673]
[http://dx.doi.org/10.1021/cr800332c] [PMID: 18986207]
[http://dx.doi.org/10.1002/cber.189302602109]
[http://dx.doi.org/10.1039/p29900001657]
[http://dx.doi.org/10.15227/orgsyn.077.0141]
[http://dx.doi.org/10.1021/ja00019a027]
[http://dx.doi.org/10.1080/00304948909356361]
[http://dx.doi.org/10.1021/jo9824596]
[http://dx.doi.org/10.1002/anie.200702313] [PMID: 17645277]
[http://dx.doi.org/10.1016/S0040-4039(01)02217-1]
[http://dx.doi.org/10.1016/j.tetlet.2008.05.017]
[http://dx.doi.org/10.1016/j.tetlet.2007.11.013]
[http://dx.doi.org/10.1002/ejoc.200600683]
[http://dx.doi.org/10.1016/j.reactfunctpolym.2005.11.011]
[http://dx.doi.org/10.1016/S0040-4039(03)00041-8]
[http://dx.doi.org/10.1002/1521-3773(20011203)40:23<4395:AID-ANIE4395>3.0.CO;2-R]
[http://dx.doi.org/10.1007/s11030-005-8105-2] [PMID: 16311811]
[http://dx.doi.org/10.1021/jo00170a070]
[http://dx.doi.org/10.1021/jo00062a040]
[http://dx.doi.org/10.1021/ja00059a052]
[http://dx.doi.org/10.1021/jo961447m]
[http://dx.doi.org/10.1021/ja900020a] [PMID: 19249829]
[http://dx.doi.org/10.1039/a906579b]
[http://dx.doi.org/10.1002/anie.200906121] [PMID: 19998303]
[http://dx.doi.org/10.1021/ja963575y]
[http://dx.doi.org/10.1021/ja9817141]
[http://dx.doi.org/10.1002/anie.200805334] [PMID: 19173267]
[http://dx.doi.org/10.1021/ja0035699] [PMID: 11457055]
[http://dx.doi.org/10.1021/jo972094+] [PMID: 11672123]
[http://dx.doi.org/10.1021/jo960461w]
[http://dx.doi.org/10.1021/ja012010l] [PMID: 11878972]
[http://dx.doi.org/10.1021/ja012011d] [PMID: 11878973]
[http://dx.doi.org/10.1016/S0040-4020(99)00342-7]
[http://dx.doi.org/10.1016/S0040-4020(01)90398-9]
[http://dx.doi.org/10.1002/1522-2675(20010228)84:2<416:AID-HLCA416>3.0.CO;2-K]
[http://dx.doi.org/10.1002/anie.200902908] [PMID: 19746498]
[http://dx.doi.org/10.1016/S0040-4039(01)00587-1]
[http://dx.doi.org/10.1016/0040-4039(94)02242-4]
[http://dx.doi.org/10.1016/S0040-4039(99)02293-5]
[http://dx.doi.org/10.1021/jo971569u]
[http://dx.doi.org/10.1055/s-2001-18759]
[http://dx.doi.org/10.1016/S0040-4039(00)60085-0]
[http://dx.doi.org/10.1055/s-2001-13353]
[http://dx.doi.org/10.1021/ja0120126] [PMID: 11878974]
[http://dx.doi.org/10.1021/ol990551y] [PMID: 10822534]
[http://dx.doi.org/10.1016/S0040-4039(01)00998-4]
[http://dx.doi.org/10.1055/s-1999-3476]
[http://dx.doi.org/10.1021/ol027518n] [PMID: 12583773]
[http://dx.doi.org/10.1016/S0040-4020(02)01379-0]
(b)Nakamura, S.; Inagaki, J.; Sugimoto, T.; Ura, Y.; Hashimoto, S. A highly stereoselective synthesis of the C10-C31 (BCDEF ring) portion of pinnatoxin A. Tetrahedron, 2002, 58(52), 10375-10386.
[http://dx.doi.org/10.1016/S0040-4020(02)01380-7]
[http://dx.doi.org/10.1002/anie.200501853] [PMID: 16124020]
[http://dx.doi.org/10.1021/jo0609374] [PMID: 17025321]
[http://dx.doi.org/10.1055/s-0029-1217136]
[http://dx.doi.org/10.1016/S0040-4039(03)00623-3]
[http://dx.doi.org/10.1016/j.tetlet.2006.12.024]
[http://dx.doi.org/10.1016/j.tetlet.2008.03.119]
[http://dx.doi.org/10.1021/jo00103a067]
[http://dx.doi.org/10.1021/acs.joc.6b00137] [PMID: 26845633]
[http://dx.doi.org/10.1080/00397911.2011.563449]
[http://dx.doi.org/10.1039/C7RA07738F]
[http://dx.doi.org/10.1055/s-2005-917077]
[http://dx.doi.org/10.1080/00397910601033641]
[http://dx.doi.org/10.1055/s-2008-1032020]
[http://dx.doi.org/10.1055/s-2008-1072730]