Catalytic Cleavage of C(sp2)–C(sp2) Bonds with Rh-Carbynoids | Zendy

Zhaofeng Wang | Zendy; Liyin Jiang | Zendy; Pau Sarró | Zendy; Marcos G. Suero | Zendy

AI Assistant Blog Pricing

Home ZAIA Blog

Open Access

Catalytic Cleavage of C(sp²)–C(sp²) Bonds with Rh-Carbynoids

Author(s) -

Zhaofeng Wang,

Liyin Jiang,

Pau Sarró,

Marcos G. Suero

Publication year - 2019

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/jacs.9b08632

Subject(s) - chemistry , carbyne , rhodium , catalysis , diazo , nucleophile , allylic rearrangement , bond cleavage , cleavage (geology) , stereochemistry , ring (chemistry) , medicinal chemistry , photochemistry , organic chemistry , carbene , geotechnical engineering , fracture (geology) , engineering

We report a catalytic strategy that generates rhodium-carbynoids by selective diazo activation of designed carbyne sources. We found that rhodium-carbynoid species provoke C( sp 2 )-C( sp 2 ) bond scission in alkenes by inserting a monovalent carbon unit between both sp 2 -hybridized carbons. This skeletal remodeling process accesses synthetically useful allyl cation intermediates that conduct to valuable allylic building blocks upon nucleophile attack. Our results rely on the formation of cyclopropyl-I (III) intermediates able to undergo electrocyclic ring-opening, following the Woodward-Hoffmann-DePuy rules.

The content you want is available to Zendy users.

Already have an account? Click here to sign in.

Having issues? You can contact us here

Accelerating Research