Choline Chloride-Based Deep Eutectic Systems in Sequential Friedländer Reaction and Palladium-Catalyzed sp3 CH Functionalization of Methyl Ketones | Zendy

Kumaraswamy Naidu Chitrala | Zendy; FazlurRahman Nawaz Khan | Zendy

Open Access

Choline Chloride-Based Deep Eutectic Systems in Sequential Friedländer Reaction and Palladium-Catalyzed sp³ CH Functionalization of Methyl Ketones

Author(s) -

Kumaraswamy Naidu Chitrala,

FazlurRahman Nawaz Khan

Publication year - 2019

Publication title -

acs omega

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.779

H-Index - 40

ISSN - 2470-1343

DOI - 10.1021/acsomega.9b00310

Subject(s) - palladium , surface modification , choline chloride , catalysis , eutectic system , chemistry , chloride , medicinal chemistry , organic chemistry , alloy

A volatile organic solvent-free and choline chloride (ChCl)-based deep eutectic system (DES)-mediated sp 3 -CH functionalization of acetophenones 1 with benzyl alcohols 2 to the corresponding α, β-saturated ketones 3 is accounted for. The domino dehydrogenation-aldol condensation (hydrogenation borrowing concept) has been successfully attempted with palladium-tetrakis(triphenylphosphine) [Pd(PPh 3 ) 4 ] catalyst-xantphos ligand combination. Furthermore, a sequential Friedländer reaction of 2-aminobenzophenone 4 and palladium-catalyzed α-alkylation of the quinolinyl methyl ketone with benzyl alcohols 2 in ChCl-based DES have been successfully investigated. The C-C bond formation through sp 3 -CH functionalization involves a wide scope of the substrates, high atom efficiency, chemoselectivity, and environmentally friendly strategy.

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