Synthesis of S-aryl thioesters via palladium-catalyzed thiocarbonylation of aryl iodides and aryl sulfonyl hydrazides

Yeojin Kim; Kwang Ho Song; Sunwoo Lee

doi:10.1039/d0qo00748j

Synthesis of S-aryl thioesters via palladium-catalyzed thiocarbonylation of aryl iodides and aryl sulfonyl hydrazides

Yeojin Kim, Kwang Ho Song, Sunwoo Lee

Department of Chemical and Biological Engineering

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

1 Citation (Scopus)

Abstract

Aryl iodides and aryl sulfonyl hydrazides were reacted with carbon monoxide in the presence of DBU and a palladium catalyst to provide optimal yields of S-aryl thioesters. Aryl sulfonyl hydrazides served as aryl thiol surrogates. Optimal results were obtained when the reaction was carried out with Pd(dba)2/dppb in toluene at 80 °C for 12 h. The methodology exhibits superior functional group tolerance, being compatible with moieties like fluoride, chloride, bromide, ester, ketone, cyanide and nitro.

Original language	English
Pages (from-to)	2938-2943
Number of pages	6
Journal	Organic Chemistry Frontiers
Volume	7
Issue number	19
DOIs	https://doi.org/10.1039/d0qo00748j
Publication status	Published - 2020 Oct 7

ASJC Scopus subject areas

Organic Chemistry

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title = "Synthesis of S-aryl thioesters via palladium-catalyzed thiocarbonylation of aryl iodides and aryl sulfonyl hydrazides",

abstract = "Aryl iodides and aryl sulfonyl hydrazides were reacted with carbon monoxide in the presence of DBU and a palladium catalyst to provide optimal yields of S-aryl thioesters. Aryl sulfonyl hydrazides served as aryl thiol surrogates. Optimal results were obtained when the reaction was carried out with Pd(dba)2/dppb in toluene at 80 °C for 12 h. The methodology exhibits superior functional group tolerance, being compatible with moieties like fluoride, chloride, bromide, ester, ketone, cyanide and nitro.",

author = "Yeojin Kim and Song, {Kwang Ho} and Sunwoo Lee",

note = "Funding Information: This research was supported by the National Research Foundation of Korea (NRF) grant funded by the Korea govern- ment (MSIP) (NRF-2017R1A2B2002929). The spectral and HRMS data were obtained from the Korea Basic Science Institute, Gwangju center and Daegu center. Publisher Copyright: {\textcopyright} 2020 the Partner Organisations.",

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doi = "10.1039/d0qo00748j",

language = "English",

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N1 - Funding Information: This research was supported by the National Research Foundation of Korea (NRF) grant funded by the Korea govern- ment (MSIP) (NRF-2017R1A2B2002929). The spectral and HRMS data were obtained from the Korea Basic Science Institute, Gwangju center and Daegu center. Publisher Copyright: © 2020 the Partner Organisations.

PY - 2020/10/7

Y1 - 2020/10/7

N2 - Aryl iodides and aryl sulfonyl hydrazides were reacted with carbon monoxide in the presence of DBU and a palladium catalyst to provide optimal yields of S-aryl thioesters. Aryl sulfonyl hydrazides served as aryl thiol surrogates. Optimal results were obtained when the reaction was carried out with Pd(dba)2/dppb in toluene at 80 °C for 12 h. The methodology exhibits superior functional group tolerance, being compatible with moieties like fluoride, chloride, bromide, ester, ketone, cyanide and nitro.

AB - Aryl iodides and aryl sulfonyl hydrazides were reacted with carbon monoxide in the presence of DBU and a palladium catalyst to provide optimal yields of S-aryl thioesters. Aryl sulfonyl hydrazides served as aryl thiol surrogates. Optimal results were obtained when the reaction was carried out with Pd(dba)2/dppb in toluene at 80 °C for 12 h. The methodology exhibits superior functional group tolerance, being compatible with moieties like fluoride, chloride, bromide, ester, ketone, cyanide and nitro.

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Synthesis of S-aryl thioesters via palladium-catalyzed thiocarbonylation of aryl iodides and aryl sulfonyl hydrazides

Abstract

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