Pd-Catalyzed MIA-Directed Methoxylation of Phenylalanines: A Combined Experimental and Computational Study

Wen-Jun Tang; Shu-Min Dai; Yue Yuan; Shuai Wang; Yu-Peng He; Fang Yu

doi:10.1055/a-2055-2313

Synthesis, Table of Contents

Synthesis 2023; 55(16): 2547-2553
DOI: 10.1055/a-2055-2313

paper

Pd-Catalyzed MIA-Directed Methoxylation of Phenylalanines: A Combined Experimental and Computational Study

Authors

Wen-Jun Tang

^aSchool of Pharmaceutical Engineering, Zhejiang Pharmaceutical University, No 666 Siming road, Fenghua District, Ningbo 315599, P. R. of China

^bState Key Laboratory of Fine Chemicals, Ningbo Institute of Dalian University of Technology, No.26 Yucai Road, Jiangbei District, Ningbo 315016, P. R. of China
Shu-Min Dai

^aSchool of Pharmaceutical Engineering, Zhejiang Pharmaceutical University, No 666 Siming road, Fenghua District, Ningbo 315599, P. R. of China

^bState Key Laboratory of Fine Chemicals, Ningbo Institute of Dalian University of Technology, No.26 Yucai Road, Jiangbei District, Ningbo 315016, P. R. of China
Yue Yuan

^aSchool of Pharmaceutical Engineering, Zhejiang Pharmaceutical University, No 666 Siming road, Fenghua District, Ningbo 315599, P. R. of China

^bState Key Laboratory of Fine Chemicals, Ningbo Institute of Dalian University of Technology, No.26 Yucai Road, Jiangbei District, Ningbo 315016, P. R. of China
Shuai Wang

^aSchool of Pharmaceutical Engineering, Zhejiang Pharmaceutical University, No 666 Siming road, Fenghua District, Ningbo 315599, P. R. of China
Yu-Peng He

^aSchool of Pharmaceutical Engineering, Zhejiang Pharmaceutical University, No 666 Siming road, Fenghua District, Ningbo 315599, P. R. of China

^bState Key Laboratory of Fine Chemicals, Ningbo Institute of Dalian University of Technology, No.26 Yucai Road, Jiangbei District, Ningbo 315016, P. R. of China
Fang Yu ∗

^aSchool of Pharmaceutical Engineering, Zhejiang Pharmaceutical University, No 666 Siming road, Fenghua District, Ningbo 315599, P. R. of China

^bState Key Laboratory of Fine Chemicals, Ningbo Institute of Dalian University of Technology, No.26 Yucai Road, Jiangbei District, Ningbo 315016, P. R. of China

^cKey Laboratory of Petrochemical Catalytic Science and Technology, Liaoning Petrochemical University, Dandong Road West 1, Fushun 113001, Liaoning, P. R. of China

Abstract

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Abstract

The direct methoxylation of substituted phenylalanines has been accomplished via methoxyiminoacyl (MIA)-mediated Pd-catalyzed C–H functionalization. A diverse array of ortho-methoxylated phenylalanine derivatives are efficiently generated in good to high yields. KIE study has shown that the oxhydryl cleavage step is the rate-limiting step. The computational data show that the participation manner of methanol has a great influence on the energy barriers of transition states during the C(sp²)–O formation stage. The pathway containing stepwise deprotonation and reductive elimination is superior to that of a concerted deprotonation-methoxylation.

Key words

methoxylation - palladium catalyst - MIA-directing group - DFT study - hydrogenation

Full Text

References

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Supplementary Material

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