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

Hui Li; Christopher P. Breen; Hyowon Seo; Timothy F. Jamison; Yuan Qing Fang; Matthew M. Bio

doi:10.1021/acs.orglett.8b00070

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

Hui Li
, Christopher P. Breen
, Hyowon Seo
, Timothy F. Jamison
, Yuan Qing Fang
, Matthew M. Bio

Materials Science and Engineering

Snapdragon Chemistry Inc.
Massachusetts Institute of Technology

Research output: Contribution to journal › Article › peer-review

159 Scopus citations

Abstract

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(sp³)-C(sp²) 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.

Original language	English
Pages (from-to)	1338-1341
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	5
DOIs	https://doi.org/10.1021/acs.orglett.8b00070
State	Published - Mar 2 2018

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title = "Ni-Catalyzed Electrochemical Decarboxylative C-C Couplings in Batch and Continuous Flow",

abstract = "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(sp3)-C(sp2) 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.",

author = "Hui Li and Breen, \{Christopher P.\} and Hyowon Seo and Jamison, \{Timothy F.\} and Fang, \{Yuan Qing\} and Bio, \{Matthew M.\}",

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doi = "10.1021/acs.orglett.8b00070",

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T1 - Ni-Catalyzed Electrochemical Decarboxylative C-C Couplings in Batch and Continuous Flow

AU - Li, Hui

AU - Breen, Christopher P.

AU - Seo, Hyowon

AU - Jamison, Timothy F.

AU - Fang, Yuan Qing

AU - Bio, Matthew M.

PY - 2018/3/2

Y1 - 2018/3/2

N2 - 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(sp3)-C(sp2) 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.

AB - 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(sp3)-C(sp2) 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.

UR - https://www.scopus.com/pages/publications/85042850898

U2 - 10.1021/acs.orglett.8b00070

DO - 10.1021/acs.orglett.8b00070

M3 - Article

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AN - SCOPUS:85042850898

SN - 1523-7060

VL - 20

SP - 1338

EP - 1341

JO - Organic Letters

JF - Organic Letters

IS - 5

ER -

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

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