Palladium-catalyzed synthesis of diaryl ketones from aldehydes and (hetero)aryl halides via C-H bond activation

Takayuki Wakaki; Takaya Togo; Daisuke Yoshidome; Yoichiro Kuninobu; Motomu Kanai

doi:10.1021/acscatal.8b00440

Palladium-catalyzed synthesis of diaryl ketones from aldehydes and (hetero)aryl halides via C-H bond activation

Takayuki Wakaki, Takaya Togo, Daisuke Yoshidome, Yoichiro Kuninobu, Motomu Kanai

Department of Fundamental Organic Chemistry

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

64 Citations (Scopus)

Abstract

We developed a palladium-catalyzed C-H transformation that enabled the synthesis of ketones from aldehydes and (hetero)aryl halides. The use of picolinamide ligands was key to achieving the transformation. Heteroaryl ketones, as well as diaryl ketones, were synthesized in good to excellent yields, even in gram-scale, using this reaction. Results of density functional theory (DFT) calculations support the C-H bond activation pathway.

Original language	English
Pages (from-to)	3123-3128
Number of pages	6
Journal	ACS Catalysis
Volume	8
Issue number	4
DOIs	https://doi.org/10.1021/acscatal.8b00440
Publication status	Published - Apr 6 2018

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)

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10.1021/acscatal.8b00440

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abstract = "We developed a palladium-catalyzed C-H transformation that enabled the synthesis of ketones from aldehydes and (hetero)aryl halides. The use of picolinamide ligands was key to achieving the transformation. Heteroaryl ketones, as well as diaryl ketones, were synthesized in good to excellent yields, even in gram-scale, using this reaction. Results of density functional theory (DFT) calculations support the C-H bond activation pathway.",

author = "Takayuki Wakaki and Takaya Togo and Daisuke Yoshidome and Yoichiro Kuninobu and Motomu Kanai",

note = "Funding Information: This work was supported in part by ERATO from JST and JSPS KAKENHI Grant No. JP 26288014. T.W. thanks JSPS for fellowships. Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

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T1 - Palladium-catalyzed synthesis of diaryl ketones from aldehydes and (hetero)aryl halides via C-H bond activation

AU - Wakaki, Takayuki

AU - Togo, Takaya

AU - Yoshidome, Daisuke

AU - Kuninobu, Yoichiro

AU - Kanai, Motomu

N1 - Funding Information: This work was supported in part by ERATO from JST and JSPS KAKENHI Grant No. JP 26288014. T.W. thanks JSPS for fellowships. Publisher Copyright: © 2018 American Chemical Society.

PY - 2018/4/6

Y1 - 2018/4/6

N2 - We developed a palladium-catalyzed C-H transformation that enabled the synthesis of ketones from aldehydes and (hetero)aryl halides. The use of picolinamide ligands was key to achieving the transformation. Heteroaryl ketones, as well as diaryl ketones, were synthesized in good to excellent yields, even in gram-scale, using this reaction. Results of density functional theory (DFT) calculations support the C-H bond activation pathway.

AB - We developed a palladium-catalyzed C-H transformation that enabled the synthesis of ketones from aldehydes and (hetero)aryl halides. The use of picolinamide ligands was key to achieving the transformation. Heteroaryl ketones, as well as diaryl ketones, were synthesized in good to excellent yields, even in gram-scale, using this reaction. Results of density functional theory (DFT) calculations support the C-H bond activation pathway.

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Palladium-catalyzed synthesis of diaryl ketones from aldehydes and (hetero)aryl halides via C-H bond activation

Abstract

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