Palladium-Catalyzed sp 3C-H Benzoxylation of Alanine Derivatives Using Aldehydes under Ambient Conditions

Kyalo Stephen Kanyiva; King Hung Nigel Tang; Jiarui Wang; Takanori Shibata

doi:10.1055/a-1422-9632

Palladium-Catalyzed sp ³C-H Benzoxylation of Alanine Derivatives Using Aldehydes under Ambient Conditions

Kyalo Stephen Kanyiva^*, King Hung Nigel Tang, Jiarui Wang, Takanori Shibata

^*Corresponding author for this work

School of Advanced Science and Engineering

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

2 Citations (Scopus)

Abstract

The Pd(II)-catalyzed sp ³C-H bond benzoxylation of N -phthaloylalanine derivatives possessing an 8-aminoquinolyl group as a directing group with aldehydes under ambient conditions is reported. When a solution of an alanine derivative and an aldehyde in a toluene/water co-solvent was reacted in the presence of palladium catalyst and tert -butyl hydroperoxide at room temperature, a benzoxylated product was formed in up to 68% yield. The protecting group of the obtained benzoxylated product was smoothly removed to afford a free amide in high yield.

Original language	English
Pages (from-to)	3085-3093
Number of pages	9
Journal	Synthesis (Germany)
Volume	53
Issue number	17
DOIs	https://doi.org/10.1055/a-1422-9632
Publication status	Published - 2021 Sept 1

Keywords

C-H bond activation
aldehydes
benzoxylation
palladium
α-amino acid derivatives

ASJC Scopus subject areas

Catalysis
Organic Chemistry

Access to Document

10.1055/a-1422-9632

Cite this

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title = "Palladium-Catalyzed sp 3C-H Benzoxylation of Alanine Derivatives Using Aldehydes under Ambient Conditions",

abstract = "The Pd(II)-catalyzed sp 3C-H bond benzoxylation of N -phthaloylalanine derivatives possessing an 8-aminoquinolyl group as a directing group with aldehydes under ambient conditions is reported. When a solution of an alanine derivative and an aldehyde in a toluene/water co-solvent was reacted in the presence of palladium catalyst and tert -butyl hydroperoxide at room temperature, a benzoxylated product was formed in up to 68% yield. The protecting group of the obtained benzoxylated product was smoothly removed to afford a free amide in high yield.",

keywords = "C-H bond activation, aldehydes, benzoxylation, palladium, α-amino acid derivatives",

author = "Kanyiva, {Kyalo Stephen} and Tang, {King Hung Nigel} and Jiarui Wang and Takanori Shibata",

note = "Funding Information: This work was supported financially by a Grant-in-Aid for Scientific Research (C) (No. 18K05114) from JSPS and Asahi Glass Research Proposal Grant (2019) for KSK.JapanSoietyforthePomotionofScience18K05114Asahi GlassFoundaion() Publisher Copyright: {\textcopyright} 2021 Georg Thieme Verlag. All rights reserved.",

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T1 - Palladium-Catalyzed sp 3C-H Benzoxylation of Alanine Derivatives Using Aldehydes under Ambient Conditions

AU - Kanyiva, Kyalo Stephen

AU - Tang, King Hung Nigel

AU - Wang, Jiarui

AU - Shibata, Takanori

N1 - Funding Information: This work was supported financially by a Grant-in-Aid for Scientific Research (C) (No. 18K05114) from JSPS and Asahi Glass Research Proposal Grant (2019) for KSK.JapanSoietyforthePomotionofScience18K05114Asahi GlassFoundaion() Publisher Copyright: © 2021 Georg Thieme Verlag. All rights reserved.

PY - 2021/9/1

Y1 - 2021/9/1

N2 - The Pd(II)-catalyzed sp 3C-H bond benzoxylation of N -phthaloylalanine derivatives possessing an 8-aminoquinolyl group as a directing group with aldehydes under ambient conditions is reported. When a solution of an alanine derivative and an aldehyde in a toluene/water co-solvent was reacted in the presence of palladium catalyst and tert -butyl hydroperoxide at room temperature, a benzoxylated product was formed in up to 68% yield. The protecting group of the obtained benzoxylated product was smoothly removed to afford a free amide in high yield.

AB - The Pd(II)-catalyzed sp 3C-H bond benzoxylation of N -phthaloylalanine derivatives possessing an 8-aminoquinolyl group as a directing group with aldehydes under ambient conditions is reported. When a solution of an alanine derivative and an aldehyde in a toluene/water co-solvent was reacted in the presence of palladium catalyst and tert -butyl hydroperoxide at room temperature, a benzoxylated product was formed in up to 68% yield. The protecting group of the obtained benzoxylated product was smoothly removed to afford a free amide in high yield.

KW - C-H bond activation

KW - aldehydes

KW - benzoxylation

KW - palladium

KW - α-amino acid derivatives

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