REVIEWS

Advances in Reactions of Iodonium Ylides

  • Minghui Tong ,
  • Xinyu Zhang ,
  • Yeming Wang ,
  • Zikun Wang
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  • a Faculty of Chemistry, Northeast Normal University, Changchun 130024
    b Institute of Chemical and Industrial Bioengineering, Jilin Engineering Normal University, Changchun 130052

Received date: 2020-06-12

  Revised date: 2020-07-15

  Online published: 2020-08-19

Supported by

the Department of Science and Technology of Jilin Province(20190103128JH); the Fundamental Research Funds for the Central Universities(2412019FZ006)

Abstract

Since the first reaction involved ylides was reported, they have been an important research direction of organic chemistry. Among them, iodonium ylides attracted considerable attentions in organic synthesis due to their unique reactivities as both iodine source and ylides. The preparation methods and structural properties of iodonium ylides are generally elaborated. Then, the reactivities of iodonium ylides are reviewed in detal, including the application of iodonium ylides as a carbene precursor in insertion reactions, cyclopropane reactions, and their development research in cycloaddition reactions, rearrangement reactions and halogenation reaction.

Cite this article

Minghui Tong , Xinyu Zhang , Yeming Wang , Zikun Wang . Advances in Reactions of Iodonium Ylides[J]. Chinese Journal of Organic Chemistry, 2021 , 41(1) : 126 -143 . DOI: 10.6023/cjoc202006021

References

[1]
Wittig G.; Geissler G. Justus Liebigs Ann. Chem. 1953, 580, 44.
[2]
Gudriniece E.; Neiland O.; Vanags G. Russ. J. Gen. Chem. 1957, 27, 2737.
[3]
Yang R.-Y.; Dai L.-X. Chin. J. Org. Chem. 1994, 14, 113.
[3]
( 杨瑞阳, 戴立信, 有机化学, 1994, 14, 113.).
[4]
Hadjiarapoglou L.; Spyroudis S.; Varvoglis A. J. Am. Chem. Soc. 1985, 107, 7178.
[5]
Zhu S.-Z.; Chen Q.-Y. J. Chem. Soc., Chem. Commun. 1990, 1459.
[6]
Hackenberg J.; Hanack M. J. Chem. Soc., Chem. Commun. 1991, 470.
[7]
Goudreau S.R.; Marcoux D.; Charette A.B. J. Org. Chem. 2009, 74, 470.
[8]
Yu J.; Liu S.S.; Cui J.; Hou X.S.; Zhang C. Org. Lett. 2012, 14, 832.
[9]
Yoshimura A.; Nemykin V.N.; Zhdankin V.V. Chem.-Eur. J. 2011, 17, 10538.
[10]
Zhu C.J.; Yoshimura A.; Ji L.; Wei Y.Y.; Nemykin V.N.; Zhdankin V.V. Org. Lett. 2012, 14, 3170.
[11]
Geary G.C.; Hope E.G.; Singh K.; Stuart A.M. RSC Adv. 2015, 5, 16501.
[12]
Doyle M.P.; Tamblyn W.H.; Bagheri V. J. Org. Chem. 1981, 46, 5094.
[13]
Padwa A.; Hornbuckle S.F. Chem. Rev. 1991, 91, 263.
[14]
Doyle M.P.; Forbes D.C.; Vasbinder M.M.; Peterson C.S. J. Am. Chem. Soc. 1998, 120, 7653.
[15]
Ochiai M.; Kitagawa Y.; Yamamoto S. J. Am. Chem. Soc. 1997, 119, 11598.
[16]
Arduengo A.J.; Kline M.; Calabrese J.C.; Davidson F. J. Am. Chem. Soc. 1991, 113, 9704.
[17]
Yang R.-Y.; Dai L.-X.; Chen C.-G. J. Chem. Soc., Chem. Commun. 1992, 1487.
[18]
Zhu S.-Z. Heteroat. Chem. 1994, 5, 9.
[19]
Nishimura T.; Iwasaki H.; Takahashi M.; Takeda M. J. Radioanal. Nucl. Chem. 2003, 255, 499.
[20]
Ivanov A.S.; Popov I.A.; Boldyrev A.I.; Zhdankin V.V. Angew. Chem., Int. Ed. 2014, 53, 9617.
[21]
Müller P.; Fernandez D. Helv. Chim. Acta 1995, 78, 947.
[22]
Moriarty R.M.; May E.J.; Prakash O. Tetrahedron Lett. 1997, 38, 4333.
[23]
Lee Y.R.; Cho B.S. Bull. Korean Chem. Soc. 2002, 23, 779.
[24]
Batsila C.; Gogonas E.P.; Kostakis G.; Hadjiarapoglou L.P. Org. Lett. 2003, 5, 1511.
[25]
Adam W.; Gogonas E.P.; Hadjiarapoglou L.P. Tetrahedron 2003, 59, 7929.
[26]
Gomes L.F.; Veiros L.F.; Maulide N.; Afonso C.A. Chem.-Eur. J. 2015, 21, 1449.
[27]
Saito M.; Kobayashi Y.; Tsuzuki S.; Takemoto Y. Angew. Chem., Int. Ed. 2017, 56, 7653.
[28]
Guo J.; Liu X.; He C.; Tan F.; Dong S.; Feng X. Chem. Commun. 2018, 54, 12254.
[29]
Moriarty R.M.; Prakash O.; Vaid R.K.; Zhao L. J. Am. Chem. Soc. 1989, 111, 6443.
[30]
Ochiai M.; Kitagawa Y. J. Org. Chem. 1999, 64, 3181.
[31]
Tao J.; Estrada C.D.; Murphy G.K. Chem. Commun. 2017, 53, 9004.
[32]
Zhang X.; Zeng R.; Feng X.; Dai Q.-S.; Liu Y.; Liu Y.-Q.; Wang Q.-W.; Li Q.-Z.; Li J.-L. Asian J. Org. Chem. 2018, 7, 2065.
[33]
Chidley T.; Murphy G.K. Org. Biomol. Chem. 2018, 16, 8486.
[34]
Chidley T.; Jameel I.; Rizwan S.; Peixoto P.A.; Pouységu L.; Quideau S.; Hopkins W.S.; Murphy G.K. Angew. Chem., Int. Ed. 2019, 58, 16959.
[35]
Hadjiarapoglou L.P. Tetrahedron Lett. 1987, 28, 4449.
[36]
Gogonas E.P.; Hadjiarapoglou L.P. Tetrahedron Lett. 2000, 41, 9299.
[37]
Paizanos K.; Charalampou D.; Kourkoumelis N.; Kalpogiannaki D.; Hadjiarapoglou L.; Spanopoulou A.; Lazarou K.; Manos M.J.; Tasiopoulos A.J.; Kubicki M.; Hadjikakou S.K. Inorg. Chem. 2012, 51, 12248.
[38]
Zhu C.; Yoshimura A.; Solntsev P.; Ji L.; Wei Y.; Nemykin V.N.; Zhdankin V.V. Chem. Commun. 2012, 48, 10108.
[39]
Koser G.F.; Yu S.-M. J. Org. Chem. 1975, 40, 1166.
[40]
Koser G.F.; Yu S.-M. J. Org. Chem. 1976, 41, 125.
[41]
Huang X.C.; Liu Y.L.; Liang Y.; Pi S.F.; Wang F.; Li J.H. Org. Lett. 2008, 10, 1525.
[42]
Pi S.-F.; Li W.-G.; Cai B.; Xiao H.-B.; Sun H.-Z. Synlett 2016, 27, 794.
[43]
Laevens B.A.; Tao J.; Murphy G.K. J. Org. Chem. 2017, 82, 11903.
[44]
Zhao Z.; Luo Y.; Liu S.; Zhang L.; Feng L.; Wang Y. Angew. Chem., Int. Ed. 2018, 57, 3792.
[45]
Xiong Y.-J.; Shi S.-Q.; Hao W.-J.; Tu S.-J.; Jiang B. Org. Chem. Front. 2018, 5, 3483.
[46]
Matveeva E.D.; Podrugina T.A.; Pavlova A.S.; Mironov A.V.; Zefirov N.S. Russ. Chem. Bull. 2008, 57, 2237.
[47]
Matveeva E.D.; Podrugina T.A.; Pavlova A.S.; Mironov A.V.; Gleiter R.; Zefirov N.S. Eur. J. Org. Chem. 2009, 2323.
[48]
Matveeva E.D.; Podrugina T.A.; Pavlova A.S.; Mironov A.V.; Borisenko A.A.; Gleiter R.; Zefirov N.S. J. Org. Chem. 2009, 74, 9428.
[49]
Matveeva E.D.; Podrugina T.A.; Taranova M.A.; Vinogradov D.S.; Gleiter R.; Zefirov N.S. J. Org. Chem. 2013, 78, 11691.
[50]
Matveeva E.D.; Podrugina T.A.; Taranova M.A.; Ivanova A.M.; Gleiter R.; Zefirov N.S. J. Org. Chem. 2012, 77, 5770.
[51]
Nekipelova T.D.; Taranova M.A.; Matveeva E.D.; Kuz’min V.A.; Zefirov N.S. Kinet. Catal. 2015, 56, 403.
[52]
Nekipelova T.D.; Podrugina T.A.; Vinogradov D.S.; Dem’yanov P.I.; Kuzmin V.A. Kinet. Catal. 2019, 60, 44.
[53]
Nekipelova T.D.; Kasparov V.V.; Kovarskii A.L.; Vorobiev A.K.; Podrugina T.A.; Vinogradov D.S.; Kuzmin V.A.; Zefirov N.S. Dokl. Phys. Chem. 2017, 474, 109.
[54]
Nekipelova T.D.; Podrugina T.A. Kinet. Catal. 2020, 61, 159.
[55]
Levina I.I.; Klimovich O.N.; Vinogradov D.S.; Podrugina T.A.; Bormotov D.S.; Kononikhin A.S.; Dement'eva O.V.; Senchikhin I.N.; Nikolaev E.N.; Kuzmin V.A.; Nekipelova T.D. J. Phys. Org. Chem. 2018, 31, e3844.
[56]
Kirmse W.; Kapps M. Chem. Ber. 1968, 101, 994.
[57]
Xu B.; Tambar U.K. J. Am. Chem. Soc. 2016, 138, 12073.
[58]
Xu B.; Gartman J.; Tambar U.K. Tetrahedron 2017, 73, 415.
[59]
Xu B.; Tambar U.K. Angew. Chem., Int. Ed. 2017, 56, 9868.
[60]
Gondo K.; Kitamura T. Molecules 2012, 17, 6625.
[61]
Murphy G.; Tao J.; Tuck T. Synthesis 2015, 48, 772.
[62]
Rotstein B.H.; Stephenson N.A.; Vasdev N.; Liang S.H. Nat. Commun. 2014, 5, 4365.
[63]
Calderwood S.; Collier T.L.; Gouverneur V.; Liang S.H.; Vasdev N. J. Fluorine Chem. 2015, 178, 249.
[64]
Stephenson N.A.; Holland J.P.; Kassenbrock A.; Yokell D.L.; Livni E.; Liang S.H.; Vasdev N. J. Nucl. Med. 2015, 56, 489.
[65]
Jung Y.W.; Gu G.; Raffel D.M. J. Labelled Compd. Radiopharm. 2019, 62, 835.
[66]
Petersen I.N.; Villadsen J.; Hansen H.D.; Madsen J.; Jensen A.A.; Gillings N.; Lehel S.; Herth M.M.; Knudsen G.M.; Kristensen J.L. Org. Biomol. Chem. 2017, 15, 4351.
[67]
Jakobsson J.E.; Riss P.J. RSC Adv. 2018, 8, 21288.
[68]
Yang Y.D.; Azuma A.; Tokunaga E.; Yamasaki M.; Shiro M.; Shibata N. J. Am. Chem. Soc. 2013, 135, 8782.
[69]
Huang Z.; Yang Y.D.; Tokunaga E.; Shibata N. Org. Lett. 2015, 17, 1094.
[70]
Huang Z.; Yang Y.-D.; Tokunaga E.; Shibata N. Asian J. Org. Chem. 2015, 4, 525.
[71]
Arimori S.; Takada M.; Shibata N. Org. Lett. 2015, 17, 1063.
[72]
Arimori S.; Takada M.; Shibata N. Dalton. Trans. 2015, 44, 19456.
[73]
Arimori S.; Matsubara O.; Takada M.; Shiro M.; Shibata N. R. Soc. Open Sci. 2016, 3, 160102.
[74]
Gondo S.; Matsubara O.; Chachignon H.; Sumii Y.; Cahard D.; Shibata N. Molecules 2019, 24, 221.
[75]
Wang J.; Jia S.; Okuyama K.; Huang Z.; Tokunaga E.; Sumii Y.; Shibata N. J. Org. Chem. 2017, 82, 11939.
[76]
Ochiai M.; Okada T.; Tada N.; Yoshimura A. Org. Lett. 2008, 10, 1425.
[77]
Zhang L.; Kong X.; Liu S.; Zhao Z.; Yu Q.; Wang W.; Wang Y. Org. Lett. 2019, 21, 2923.
[78]
Zhang L.; Zhao Z.; Wang W.; Liu S.; Wang Y. Org. Lett. 2019, 21, 9171.
[79]
Gazis T.A.; Mohajeri Thaker B.A.J.; Willcox D.; Ould D.M.C.; Wenz J.; Rawson J.M.; Hill M.S.; Wirth T.; Melen R.L. Chem. Commun. 2020, 56, 3345.
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