Palladium-catalyzed benzylic substitution of benzyl carbonates with phosphorus nucleophiles

Yusuke Makida; Kazumi Usui; Satoshi Ueno; Ryoichi Kuwano

doi:10.1246/cl.170901

Palladium-catalyzed benzylic substitution of benzyl carbonates with phosphorus nucleophiles

Yusuke Makida, Kazumi Usui, Satoshi Ueno, Ryoichi Kuwano

Multidisciplinary chemistry

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

15 Citations (Scopus)

Abstract

A wide range of benzyl carbonates reacted with dimethyl phosphonate or diphenylphosphine oxide in the presence of the palladium catalyst, [Pd(η³-allyl)Cl]₂DPEphos, to give dimethyl benzylphosphonates and benzyldiphenylphosphine oxides in high yields. The catalytic phosphonylation was applied to the one-pot synthesis of alkenes from the benzyl esters.

Original language	English
Pages (from-to)	1814-1817
Number of pages	4
Journal	Chemistry Letters
Volume	46
Issue number	12
DOIs	https://doi.org/10.1246/cl.170901
Publication status	Published - 2017

All Science Journal Classification (ASJC) codes

Chemistry(all)

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10.1246/cl.170901

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title = "Palladium-catalyzed benzylic substitution of benzyl carbonates with phosphorus nucleophiles",

abstract = "A wide range of benzyl carbonates reacted with dimethyl phosphonate or diphenylphosphine oxide in the presence of the palladium catalyst, [Pd(η3-allyl)Cl]2DPEphos, to give dimethyl benzylphosphonates and benzyldiphenylphosphine oxides in high yields. The catalytic phosphonylation was applied to the one-pot synthesis of alkenes from the benzyl esters.",

author = "Yusuke Makida and Kazumi Usui and Satoshi Ueno and Ryoichi Kuwano",

note = "Funding Information: This work was supported by Grant-in-Aid for Young Scientists (B) (JSPS KAKENHI Grant Number JP17K14450). We thank the Cooperative Research Program “Network Joint Research for Material and Devices” for HRMS measurements.",

year = "2017",

doi = "10.1246/cl.170901",

language = "English",

volume = "46",

pages = "1814--1817",

journal = "Chemistry Letters",

issn = "0366-7022",

publisher = "The Chemical Society of Japan",

number = "12",

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TY - JOUR

T1 - Palladium-catalyzed benzylic substitution of benzyl carbonates with phosphorus nucleophiles

AU - Makida, Yusuke

AU - Usui, Kazumi

AU - Ueno, Satoshi

AU - Kuwano, Ryoichi

N1 - Funding Information: This work was supported by Grant-in-Aid for Young Scientists (B) (JSPS KAKENHI Grant Number JP17K14450). We thank the Cooperative Research Program “Network Joint Research for Material and Devices” for HRMS measurements.

PY - 2017

Y1 - 2017

N2 - A wide range of benzyl carbonates reacted with dimethyl phosphonate or diphenylphosphine oxide in the presence of the palladium catalyst, [Pd(η3-allyl)Cl]2DPEphos, to give dimethyl benzylphosphonates and benzyldiphenylphosphine oxides in high yields. The catalytic phosphonylation was applied to the one-pot synthesis of alkenes from the benzyl esters.

AB - A wide range of benzyl carbonates reacted with dimethyl phosphonate or diphenylphosphine oxide in the presence of the palladium catalyst, [Pd(η3-allyl)Cl]2DPEphos, to give dimethyl benzylphosphonates and benzyldiphenylphosphine oxides in high yields. The catalytic phosphonylation was applied to the one-pot synthesis of alkenes from the benzyl esters.

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U2 - 10.1246/cl.170901

DO - 10.1246/cl.170901

M3 - Article

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VL - 46

SP - 1814

EP - 1817

JO - Chemistry Letters

JF - Chemistry Letters

IS - 12

ER -

Palladium-catalyzed benzylic substitution of benzyl carbonates with phosphorus nucleophiles

Abstract

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