Ni-Catalyzed Electrochemical Decarboxylative C–C Couplings in Batch and Continuous Flow | Zendy

Hui Li | Zendy; C. Breen | Zendy; Hyowon Seo | Zendy; Timothy F. Jamison | Zendy; YuanQing Fang | Zendy; Matthew M. Bio | Zendy

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Ni-Catalyzed Electrochemical Decarboxylative C–C Couplings in Batch and Continuous Flow

Author(s) -

Hui Li,

C. Breen,

Hyowon Seo,

Timothy F. Jamison,

YuanQing Fang,

Matthew M. Bio

Publication year - 2018

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.8b00070

Subject(s) - chemistry , electrochemistry , halide , combinatorial chemistry , aryl , catalysis , amine gas treating , nickel , substrate (aquarium) , organic chemistry , electrode , geology , alkyl , oceanography

An electrochemically driven, nickel-catalyzed reductive coupling of N-hydroxyphthalimide esters with aryl halides is reported. The reaction proceeds under mild conditions in a divided electrochemical cell and employs a tertiary amine as the reductant. This decarboxylative C(sp 3 )-C(sp 2 ) bond-forming transformation exhibits excellent substrate generality and functional group compatibility. An operationally simple continuous-flow version of this transformation using a commercial electrochemical flow reactor represents a robust and scalable synthesis of value added coupling process.

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