Chemoselective Homologation–Deoxygenation Strategy Enabling the Direct Conversion of Carbonyls into (n+1)-Halomethyl-Alkanes | Zendy

Margherita Miele | Zendy; Andrea Citarella | Zendy; Thierry Langer | Zendy; Ernst Urban | Zendy; Martin Zehl | Zendy; Wolfgang Hölzer | Zendy; Laura Ielo | Zendy; Vittorio Pace | Zendy

Open Access

Chemoselective Homologation–Deoxygenation Strategy Enabling the Direct Conversion of Carbonyls into (n+1)-Halomethyl-Alkanes

Author(s) -

Margherita Miele,

Andrea Citarella,

Thierry Langer,

Ernst Urban,

Martin Zehl,

Wolfgang Hölzer,

Laura Ielo,

Vittorio Pace

Publication year - 2020

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.0c02831

Subject(s) - chemistry , nucleophile , carbenoid , carbanion , deoxygenation , electrophile , alkyl , halide , tributyltin hydride , carbon fibers , organic chemistry , combinatorial chemistry , medicinal chemistry , catalysis , rhodium , materials science , composite number , composite material

The sequential installation of a carbenoid and a hydride into a carbonyl, furnishing halomethyl alkyl derivatives, is reported. Despite the employment of carbenoids as nucleophiles in reactions with carbon-centered electrophiles, sp 3 -type alkyl halides remain elusive materials for selective one-carbon homologations. Our tactic levers on using carbonyls as starting materials and enables uniformly high yields and chemocontrol. The tactic is flexible and is not limited to carbenoids. Also, diverse carbanion-like species can act as nucleophiles, thus making it of general applicability.

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