Palladium-Catalyzed Reductive Conversion of Acyl Fluorides via Ligand-Controlled Decarbonylation

Yohei Ogiwara; Yuka Sakurai; Hiroyuki Hattori; Norio Sakai

doi:10.1021/acs.orglett.8b01582

Palladium-Catalyzed Reductive Conversion of Acyl Fluorides via Ligand-Controlled Decarbonylation

Yohei Ogiwara, Yuka Sakurai, Hiroyuki Hattori, Norio Sakai

Department of Pure and Applied Chemistry

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

87 Citations (Scopus)

Abstract

Ligand-controlled non-decarbonylative and decarbonylative conversions of acyl fluorides were developed using a Pd(OAc)₂/Et₃SiH combination. When tricyclohexylphosphine (PCy₃) was used as the ligand, aldehydes were obtained as simple reductive conversion products. The use of 1,2-bis(dicyclohexylphosphino)ethane (Cy₂P(CH₂)₂PCy₂, DCPE) as the ligand, however, favored the formation of hydrocarbons, which are decarbonylative reduction products.

Original language	English
Pages (from-to)	4204-4208
Number of pages	5
Journal	Organic Letters
Volume	20
Issue number	14
DOIs	https://doi.org/10.1021/acs.orglett.8b01582
Publication status	Published - 20 Jul 2018

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abstract = "Ligand-controlled non-decarbonylative and decarbonylative conversions of acyl fluorides were developed using a Pd(OAc)2/Et3SiH combination. When tricyclohexylphosphine (PCy3) was used as the ligand, aldehydes were obtained as simple reductive conversion products. The use of 1,2-bis(dicyclohexylphosphino)ethane (Cy2P(CH2)2PCy2, DCPE) as the ligand, however, favored the formation of hydrocarbons, which are decarbonylative reduction products.",

author = "Yohei Ogiwara and Yuka Sakurai and Hiroyuki Hattori and Norio Sakai",

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AU - Ogiwara, Yohei

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AU - Hattori, Hiroyuki

AU - Sakai, Norio

PY - 2018/7/20

Y1 - 2018/7/20

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AB - Ligand-controlled non-decarbonylative and decarbonylative conversions of acyl fluorides were developed using a Pd(OAc)2/Et3SiH combination. When tricyclohexylphosphine (PCy3) was used as the ligand, aldehydes were obtained as simple reductive conversion products. The use of 1,2-bis(dicyclohexylphosphino)ethane (Cy2P(CH2)2PCy2, DCPE) as the ligand, however, favored the formation of hydrocarbons, which are decarbonylative reduction products.

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ER -

Palladium-Catalyzed Reductive Conversion of Acyl Fluorides via Ligand-Controlled Decarbonylation

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