The generation of heteroatom-centred radicals followed by intramolecular 1,5-HAT and functionalisation of the translocated carbon-centred radical is an efficient way to functionalize chemo- and regio-selectively the remote unactivated C(sp3)–H bond.
An approach for iodofluoroalkylation of unactivated alkynes and alkenes facilitated by an earth‐abundant and inexpensive manganese catalyst, Mn2(CO)10, is reported. This protocol employs visible light as the energy input and shows a wide substrate scope and high functional‐group compatibility. A variety of synthetically useful fluoroalkylated alkyl and alkenyl iodides can be prepared in moderate to excellent yields. The reaction features high efficiency, operational simplicity, scalability, as well as excellent chemo‐, regio‐, and E/Z selectivities.
Selective three‐component 1,2‐diamination of 1,3‐dienes with concurrent introduction of two orthogonally protected amino groups remains unknown despite its significant synthetic potential. We report herein that reaction of conjugated dienes with N‐aminopyridinium salts and TMSNCS affords 1,2‐aminoisothiocyanation products in a highly chemo‐ and regio‐selective manner under mild photoredox catalytic conditions. Mechanistic studies indicate that the facile isomerization of allyl thiocyanates to allyl isothiocyanates under photocatalytic conditions is responsible for the selective formation of the observed products. The mild isomerization protocol is expected to find applications in the synthesis of allyl isothiocyanates in a broad sense.
Selective
C(sp3)–H isothiocyanation represents
a significant strategy for the synthesis of isothiocyanate derivatives.
We report herein an electrochemical benzylic isothiocyanation in a
highly chemo- and site-selective manner under external oxidant-free
conditions. The high chemoselectivity is attributed to the facile in situ isomerization of benzylic thiocyanates to isothiocyanates.
Notably, the method exhibits high functional group compatibility and
is suitable for late-stage functionalization of bioactive molecules.
The scalable reduction of sulfoxides to sulfides in a sustainable way remains an unmet challenge. This report discloses an electrochemical reduction of sulfoxides on a large scale (> 10 g)...
A novel copper-catalyzed tandem C-S/C-C bond-forming reaction of 2-biaryl isothiocyanates with diaryliodonium salts was developed. This is the first general approach to synthesize phenanthridines from 2-biaryl isothiocyanates. This methodology has been successfully applied to the synthesis of trisphaeridine.
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