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Review
. 2018 Jul 18:14:1813-1825.
doi: 10.3762/bjoc.14.154. eCollection 2018.

Recent advances in hypervalent iodine(III)-catalyzed functionalization of alkenes

Xiang Li  1 , Pinhong Chen  1 , Guosheng Liu  1
Affiliations
Review

Recent advances in hypervalent iodine(III)-catalyzed functionalization of alkenes

Xiang Li et al. Beilstein J Org Chem. .

Abstract

Hypervalent iodine(III) reagents have been well-developed and widely utilized in functionalization of alkenes, however, generally either stoichiometric amounts of iodine(III) reagents are required or stoichiometric oxidants such as mCPBA are employed to in situ generate iodine(III) species. In this review, recent developments of hypervalent iodine(III)-catalyzed functionalization of alkenes and asymmetric reactions using a chiral iodoarene are summarized.

Keywords: asymmetric catalysis; functionalization of alkenes; hypervalent iodine(III).

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Figures

Figure 1
Figure 1
The structures of hypervalent iodine (III) reagents [8].
Scheme 1
Scheme 1
Hypervalent iodine(III)-catalyzed functionalization of alkenes.
Scheme 2
Scheme 2
Catalytic sulfonyloxylactonization of alkenoic acids [43].
Scheme 3
Scheme 3
Catalytic diacetoxylation of alkenes [46].
Scheme 4
Scheme 4
Intramolecular asymmetric dioxygenation of alkenes [48,50].
Scheme 5
Scheme 5
Intermolecular asymmetric diacetoxylation of styrenes [52].
Scheme 6
Scheme 6
Diacetoxylation of alkenes with ester groups containing catalysts 17 [55].
Scheme 7
Scheme 7
Intramolecular diamination of alkenes [56].
Scheme 8
Scheme 8
Intramolecular asymmetric diamination of alkenes [57].
Scheme 9
Scheme 9
Intermolecular asymmetric diamination of alkenes [58].
Scheme 10
Scheme 10
Iodoarene-catalyzed aminofluorination of alkenes [–61].
Scheme 11
Scheme 11
Iodoarene-catalyzed aminofluorination of alkenes [62].
Scheme 12
Scheme 12
Catalytic difluorination of alkenes with Selectfluor [63].
Scheme 13
Scheme 13
Iodoarene-catalyzed 1,2-difluorination of alkenes [64].
Scheme 14
Scheme 14
Iodoarene-catalyzed asymmetric fluorination of styrenes [–65].
Scheme 15
Scheme 15
Gem-difluorination of styrenes [67].
Scheme 16
Scheme 16
Asymmetric gem-difluorination of cinnamic acid derivatives [68].
Scheme 17
Scheme 17
Oxyarylation of alkenes [71].
Scheme 18
Scheme 18
Asymmetric oxidative rearrangements of alkenes [72].
Scheme 19
Scheme 19
Bromolactonization of alkenes [75].
Scheme 20
Scheme 20
Bromination of alkenes [–78].
Scheme 21
Scheme 21
Cooperative strategy for the carbonylation of alkenes [79].
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References

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