Electrolytic C-H Oxygenation via Oxidatively Induced Reductive Elimination in Rh Catalysis

Seongho Jin; Jinwoo Kim; Dongwook Kim; Jung Woo Park; Sukbok Chang

doi:10.1021/acscatal.1c01670

Electrolytic C-H Oxygenation via Oxidatively Induced Reductive Elimination in Rh Catalysis

Seongho Jin, Jinwoo Kim, Dongwook Kim, Jung Woo Park, Sukbok Chang

Dept. of Fine Chemistry

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

44 Scopus citations

Abstract

Herein, we describe the development of a Rh-catalyzed C-H acyloxylation under mild electrolytic conditions. Anodic oxidation of a key rhodacyclic carboxylate intermediate was found to enable the product-releasing C-O bond-forming reductive elimination process. An accumulation of carboxylate near the electrode surface was rationalized to further induce the desired C-O bond formation, allowing an ambient catalytic C-H oxygenation using stoichiometric amounts of readily accessible carboxylic acid coupling partners.

Original language	English
Pages (from-to)	6590-6595
Number of pages	6
Journal	ACS Catalysis
Volume	11
DOIs	https://doi.org/10.1021/acscatal.1c01670
State	Published - 2021

Keywords

C-H activation
C-O bond formation
electrochemistry
high-valent pathway
reductive elimination

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10.1021/acscatal.1c01670

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title = "Electrolytic C-H Oxygenation via Oxidatively Induced Reductive Elimination in Rh Catalysis",

abstract = "Herein, we describe the development of a Rh-catalyzed C-H acyloxylation under mild electrolytic conditions. Anodic oxidation of a key rhodacyclic carboxylate intermediate was found to enable the product-releasing C-O bond-forming reductive elimination process. An accumulation of carboxylate near the electrode surface was rationalized to further induce the desired C-O bond formation, allowing an ambient catalytic C-H oxygenation using stoichiometric amounts of readily accessible carboxylic acid coupling partners.",

keywords = "C-H activation, C-O bond formation, electrochemistry, high-valent pathway, reductive elimination",

author = "Seongho Jin and Jinwoo Kim and Dongwook Kim and Park, \{Jung Woo\} and Sukbok Chang",

note = "Publisher Copyright: {\textcopyright} 2021 American Chemical Society.",

year = "2021",

doi = "10.1021/acscatal.1c01670",

language = "English",

volume = "11",

pages = "6590--6595",

journal = "ACS Catalysis",

issn = "2155-5435",

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T1 - Electrolytic C-H Oxygenation via Oxidatively Induced Reductive Elimination in Rh Catalysis

AU - Jin, Seongho

AU - Kim, Jinwoo

AU - Kim, Dongwook

AU - Park, Jung Woo

AU - Chang, Sukbok

PY - 2021

Y1 - 2021

N2 - Herein, we describe the development of a Rh-catalyzed C-H acyloxylation under mild electrolytic conditions. Anodic oxidation of a key rhodacyclic carboxylate intermediate was found to enable the product-releasing C-O bond-forming reductive elimination process. An accumulation of carboxylate near the electrode surface was rationalized to further induce the desired C-O bond formation, allowing an ambient catalytic C-H oxygenation using stoichiometric amounts of readily accessible carboxylic acid coupling partners.

AB - Herein, we describe the development of a Rh-catalyzed C-H acyloxylation under mild electrolytic conditions. Anodic oxidation of a key rhodacyclic carboxylate intermediate was found to enable the product-releasing C-O bond-forming reductive elimination process. An accumulation of carboxylate near the electrode surface was rationalized to further induce the desired C-O bond formation, allowing an ambient catalytic C-H oxygenation using stoichiometric amounts of readily accessible carboxylic acid coupling partners.

KW - C-H activation

KW - C-O bond formation

KW - electrochemistry

KW - high-valent pathway

KW - reductive elimination

UR - http://www.scopus.com/inward/record.url?scp=85108194877&partnerID=8YFLogxK

U2 - 10.1021/acscatal.1c01670

DO - 10.1021/acscatal.1c01670

M3 - Article

AN - SCOPUS:85108194877

SN - 2155-5435

VL - 11

SP - 6590

EP - 6595

JO - ACS Catalysis

JF - ACS Catalysis

ER -

Electrolytic C-H Oxygenation via Oxidatively Induced Reductive Elimination in Rh Catalysis

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Keywords

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