1360187-87-6Relevant academic research and scientific papers
Traceless directing groups in radical cascades: From oligoalkynes to fused helicenes without tethered initiators
Pati, Kamalkishore,Gomes, Gabriel Dos Passos,Harris, Trevor,Hughes, Audrey,Phan, Hoa,Banerjee, Tanmay,Hanson, Kenneth,Alabugin, Igor V.
, p. 1165 - 1180 (2015)
We report the first example of a traceless directing group in a radical cascade. The chemo- and regioselectivity of the initial attack in skipped oligoalkynes is controlled by propargyl OR moiety. Radical translocations lead to the boomerang return of the radical center to the site of initial attack where it assists the elimination of the directing functionality via β-scission in the last step of the cascade. The Bu3Sn moiety continues further via facile reactions with electrophiles as well as Stille and Suzuki cross-coupling reactions. This selective radical transformation opens a new approach for the controlled transformation of skipped oligoalkynes into polycyclic ribbons of tunable dimensions. (Chemical Equation Presented).
TRACELESS DIRECTING GROUPS IN RADICAL CASCADES: FROM OLIGOALKYNES TO FUSED HELICENES WITHOUT TETHERED INITATORS
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, (2016/06/13)
The present disclosure is directed to a traceless directing group in a radical cascade. The chemo- and regioselectivity of the initial attack in skipped oligoalkynes is controlled by a propargyl alkoxy moiety. Radical translocations lead to the boomerang return of radical center to the site of initial attack where it assists to the elimination of the directing functionality via β-scission in the last step of the cascade. In some aspects, the reaction of the present invention is catalyzed by a stannane moiety, which allows further via facile reactions with electrophiles as well as Stille and Suzuki cross-coupling reactions. This selective radical transformation opens a new approach for the controlled transformation of skipped oligoalkynes into polycyclic ribbons of tunable dimensions.
