Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 137, Issue 3, Pages 1165-1180Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja510563d
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Funding
- National Science Foundation [CHE-1152491, CHE-1213578]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1213578, 1152491] Funding Source: National Science Foundation
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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 beta-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.
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