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Review
. 2018 Nov 7;5(11):181389.
doi: 10.1098/rsos.181389. eCollection 2018 Nov.

ROTf-induced annulation of heteroatom reagents and unsaturated substrates leading to cyclic compounds

Song Zou  1 , Sheng Wang  1 , Chanjuan Xi  1   2
Affiliations
Review

ROTf-induced annulation of heteroatom reagents and unsaturated substrates leading to cyclic compounds

Song Zou et al. R Soc Open Sci. .

Abstract

The development of metal-free organic reactions is one of the hotspots in the synthesis of cyclic compounds. ROTf (alkyl trifluoromethanesulfonates), due to their good electrophilicity, are powerful alkylating reagents at heteroatoms such as nitrogen, oxygen, sulfur and phosphorus to induce an electrophilic centre for carbon-carbon or carbon-heteroatom bond formation. Inspired by this chemistry, a variety of research concentrating on heterocycles synthesis has been carried out. In this review, we mainly summarize the ROTf-induced annulation of heteroatom reagents such as nitriles, carbodiimides, azobenzenes, isothiocyanates, aldehydes, isocyanates and phosphaalkene with themselves or alkynes to afford cyclic compounds.

Keywords: annulation; cyclic compounds; heteroatom reagents; trifluoromethanesulfonates.

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Conflict of interest statement

We declare we have no competing interests.

Figures

Scheme 1.
Scheme 1.
ROTf-mediated reactions.
Scheme 2.
Scheme 2.
MeOTf-induced cyclization of arylnitriles and alkynes.
Scheme 3.
Scheme 3.
ROTf-induced cyclization of alkylnitriles and alkynes.
Scheme 4.
Scheme 4.
MeOTf-induced cyclization of alkylnitriles and diarylalkynes.
Scheme 5.
Scheme 5.
ROTf-induced cyclization of diarylcarbodiimides.
Scheme 6.
Scheme 6.
ROTf-induced cyclization of diarylcarbodiimides and dialkylcarbodiimides.
Scheme 7.
Scheme 7.
ROTf-induced cyclization of azobenzenes.
Scheme 8.
Scheme 8.
ROTf-induced cyclization of arylisothiocyanates and arylalkynes.
Scheme 9.
Scheme 9.
ROTf-induced annulation of alkylisothiocyanates and arylalkynes.
Scheme 10.
Scheme 10.
MeOTf-induced intramolecular cyclization of isothiocyanates.
Scheme 11.
Scheme 11.
MeOTf-induced cyclization of aldehyde with arylalkynes.
Scheme 12.
Scheme 12.
MeOTf-induced cyclization of arylisocyanates and arylalkynes.
Scheme 13.
Scheme 13.
MeOTf-induced cyclization with o-arylanilines and CO2.
Scheme 14.
Scheme 14.
MeOTf-induced cyclization with phosphaalkenes.
See this image and copyright information in PMC

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