Palladium-Catalyzed Reactions of Allylic Boronic Esters with Nucleophiles: Novel Umpolung Reactivity

Phillip J. Unsworth; Lorenz E. Löffler; Adam Noble; Varinder K. Aggarwal

doi:10.1055/s-0034-1380869

Palladium-Catalyzed Reactions of Allylic Boronic Esters with Nucleophiles: Novel Umpolung Reactivity

Phillip J. Unsworth
, Lorenz E. Löffler
, Adam Noble
, Varinder K. Aggarwal^*

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

5 Citations (Scopus)

Abstract

Oxidative palladium-catalyzed reaction conditions have been developed to allow for regioselective and stereoselective coupling of allylic boronic esters with a range of carbon-, oxygen-, and nitrogen-based nucleophiles. Studies into the mechanism of the reaction have shown that the key transmetalation step occurs with retention of stereochemistry, since overall inversion is observed.

Original language	English
Article number	st-2015-b0205-l
Pages (from-to)	1567-1572
Number of pages	6
Journal	Synlett
Volume	26
Issue number	11
DOIs	https://doi.org/10.1055/s-0034-1380869
Publication status	Published - 1 Jul 2015

Research Groups and Themes

BCS and TECS CDTs
Organic & Biological

Keywords

allylation
boronic ester
oxidative coupling
palladium
umpolung

Access to Document

10.1055/s-0034-1380869

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Cite this

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title = "Palladium-Catalyzed Reactions of Allylic Boronic Esters with Nucleophiles: Novel Umpolung Reactivity",

abstract = "Oxidative palladium-catalyzed reaction conditions have been developed to allow for regioselective and stereoselective coupling of allylic boronic esters with a range of carbon-, oxygen-, and nitrogen-based nucleophiles. Studies into the mechanism of the reaction have shown that the key transmetalation step occurs with retention of stereochemistry, since overall inversion is observed.",

keywords = "allylation, boronic ester, oxidative coupling, palladium, umpolung",

author = "Unsworth, \{Phillip J.\} and L{\"o}ffler, \{Lorenz E.\} and Adam Noble and Aggarwal, \{Varinder K.\}",

year = "2015",

month = jul,

day = "1",

doi = "10.1055/s-0034-1380869",

language = "English",

volume = "26",

pages = "1567--1572",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "11",

}

TY - JOUR

T1 - Palladium-Catalyzed Reactions of Allylic Boronic Esters with Nucleophiles

T2 - Novel Umpolung Reactivity

AU - Unsworth, Phillip J.

AU - Löffler, Lorenz E.

AU - Noble, Adam

AU - Aggarwal, Varinder K.

PY - 2015/7/1

Y1 - 2015/7/1

N2 - Oxidative palladium-catalyzed reaction conditions have been developed to allow for regioselective and stereoselective coupling of allylic boronic esters with a range of carbon-, oxygen-, and nitrogen-based nucleophiles. Studies into the mechanism of the reaction have shown that the key transmetalation step occurs with retention of stereochemistry, since overall inversion is observed.

AB - Oxidative palladium-catalyzed reaction conditions have been developed to allow for regioselective and stereoselective coupling of allylic boronic esters with a range of carbon-, oxygen-, and nitrogen-based nucleophiles. Studies into the mechanism of the reaction have shown that the key transmetalation step occurs with retention of stereochemistry, since overall inversion is observed.

KW - allylation

KW - boronic ester

KW - oxidative coupling

KW - palladium

KW - umpolung

UR - https://www.scopus.com/pages/publications/84931955362

U2 - 10.1055/s-0034-1380869

DO - 10.1055/s-0034-1380869

M3 - Article (Academic Journal)

AN - SCOPUS:84931955362

SN - 0936-5214

VL - 26

SP - 1567

EP - 1572

JO - Synlett

JF - Synlett

IS - 11

M1 - st-2015-b0205-l

ER -

Palladium-Catalyzed Reactions of Allylic Boronic Esters with Nucleophiles: Novel Umpolung Reactivity

Abstract

Research Groups and Themes

Keywords

Access to Document

Handle.net

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3-month Core Capability for Chemistry Research

Changing the Synthesis Landscape with Boron at the Helm: from Chiral Organometallics to Assembly Line Synthesis

Cite this

Palladium-Catalyzed Reactions of Allylic Boronic Esters with Nucleophiles: Novel Umpolung Reactivity

Abstract

Research Groups and Themes

Keywords

Access to Document

Handle.net

Other files and links

Fingerprint

Projects

3-month Core Capability for Chemistry Research

Changing the Synthesis Landscape with Boron at the Helm: from Chiral Organometallics to Assembly Line Synthesis

Cite this