Photocatalytic direct intermolecular addition of 1,3-dithianes

Abstract

Graphical AbstractA direct intermolecular radical addition of 1,3-dithianes to alkenes has been accomplished via visible-light mediated photocatalysis.

Electrophilic Trapping of Semibenzenes

“…Finally, the reaction with 1,3-benzo dithiolylium tetrafluoroborate allows for the introduction of a versatile functional group, which can act as an intermediate toward more complex scaffolds. , An example of this is shown in Scheme , where we demonstrate the versatility of a dithiane-naphthalene core. Specifically, 8f and 8k were subjected to lithiation with n BuLi, followed by the addition of alkyl and benzyl electrophiles, yielding the alkylated ( 9 ) products in good yields.…”

Reactions of 2‐Aryl‐1,3‐Dithianes and [1.1.1]Propellane

“…A second mechanistic pathway, involving a single‐electron transfer from INT1 to [1.1.1]propellane was also considered. This pathway would proceed through an electron transfer from INT1 to [1.1.1]propellane (see the Supporting Information for details).…”

Acetal Radicals: Synthetic Access and Applications

“…[99] A direct photocatalytic addition into Michael acceptors and alkenes from 1,3-benzodithiole has been demonstrated under very mild conditions (Scheme 16). [100] It is notable that the reaction proceeds in the presence of fluorescent white light at an ambient temperature, and no additional HAT reagent was necessary for the key abstraction needed for radical formation. The authors note that their reaction design was dependent on select dithianes and had to be carefully optimized.…”