Traceless Directing Groups in Radical Cascades: From Oligoalkynes to Fused Helicenes without Tethered Initiators | Zendy

Kamalkishore Pati | Zendy; Gabriel dos Passos Gomes | Zendy; Trevor Harris | Zendy; Audrey Hughes | Zendy; Hoa Phan | Zendy; Tanmay Banerjee | Zendy; Kenneth Hanson | Zendy; Igor V. Alabugin | Zendy

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Traceless Directing Groups in Radical Cascades: From Oligoalkynes to Fused Helicenes without Tethered Initiators

Author(s) -

Kamalkishore Pati,

Gabriel dos Passos Gomes,

Trevor Harris,

Audrey Hughes,

Hoa Phan,

Tanmay Banerjee,

Kenneth Hanson,

Igor V. Alabugin

Publication year - 2014

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/ja510563d

Subject(s) - chemistry , moiety , stille reaction , electrophile , regioselectivity , propargyl , radical cyclization , cascade reaction , cascade , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , chromatography

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.

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