Beilstein J. Org. Chem.2021,17, 2102–2122, doi:10.3762/bjoc.17.137
to re-participate in the reaction (Scheme 15b).
There are several uses of sulfoxides as a thiol-free sulfur source for introducing sulfur at the indole C3 position [84][85][86]. In 2013, Hamashima reported a synthesis of di(indol-3-yl)sulfide (105a) by reacting indole with DMSO in the presence of
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Graphical Abstract
Scheme 1:
Synthesis of 2,2’-bis(indole)borinic ester 3.
Beilstein J. Org. Chem.2019,15, 378–387, doi:10.3762/bjoc.15.34
; sulfoxide; thiol-free; Introduction
Throughout the years, several strategies have been developed to build up organic compounds bearing a sulfide moiety [1][2]. Often, thiols (or the corresponding thiolate anions) are employed as nucleophilic sulfur reagents in order to react with a suitable electrophile [3
][4], however, there are certain negative aspects of thiols that need to be taken into account (i.e., foul smell, easy oxidation into disulfide, participation as donors in one-electron events, reaction with olefins through ene-type reactions, etc) [5][6][7][8]. Hence, the development of thiol-free
further preparation of valuable ketosulfoxides and ketosulfones.
Selected examples of valuable β-ketosulfides. A: bioactive synthetic compounds, B: natural products.
Time-course plot for the CAL-B catalysed hydrolysis of 1a.
Different strategies for the preparation of β-ketosulfides.
Thiol-free