Amide Acetal in Palladium-Catalyzed Allylation with Allylic Alcohols under Neutral Conditions

Yongseok Kwon; Jaehyun Jung; Jae Hyun Kim; Woo Jung Kim; Sanghee Kim

doi:10.1002/ajoc.201600578

Amide Acetal in Palladium-Catalyzed Allylation with Allylic Alcohols under Neutral Conditions

Yongseok Kwon, Jaehyun Jung, Jae Hyun Kim, Woo Jung Kim, Sanghee Kim

Seoul National University

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

8 Scopus citations

Abstract

A mild and efficient palladium-catalyzed allylation reaction with allylic alcohols is described. The in situ activation of the allylic alcohol is achieved by using N,N-dimethylacetamide dimethyl acetal and a simple palladium catalyst (i.e., Pd(PPh₃)₄). The reaction system does not require acid or base additives or specially designed ligands. In addition to carbon nucleophiles, nitrogen and oxygen nucleophiles can also be used with the allylic alcohol in this transformation.

Original language	English
Pages (from-to)	520-526
Number of pages	7
Journal	Asian Journal of Organic Chemistry
Volume	6
Issue number	5
DOIs	https://doi.org/10.1002/ajoc.201600578
State	Published - May 2017
Externally published	Yes

Keywords

alcohols
allylation
amines
palladium
synthetic methods

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10.1002/ajoc.201600578

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title = "Amide Acetal in Palladium-Catalyzed Allylation with Allylic Alcohols under Neutral Conditions",

abstract = "A mild and efficient palladium-catalyzed allylation reaction with allylic alcohols is described. The in situ activation of the allylic alcohol is achieved by using N,N-dimethylacetamide dimethyl acetal and a simple palladium catalyst (i.e., Pd(PPh3)4). The reaction system does not require acid or base additives or specially designed ligands. In addition to carbon nucleophiles, nitrogen and oxygen nucleophiles can also be used with the allylic alcohol in this transformation.",

keywords = "alcohols, allylation, amines, palladium, synthetic methods",

author = "Yongseok Kwon and Jaehyun Jung and Kim, \{Jae Hyun\} and Kim, \{Woo Jung\} and Sanghee Kim",

note = "Publisher Copyright: {\textcopyright} 2017 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2017",

month = may,

doi = "10.1002/ajoc.201600578",

language = "English",

volume = "6",

pages = "520--526",

journal = "Asian Journal of Organic Chemistry",

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T1 - Amide Acetal in Palladium-Catalyzed Allylation with Allylic Alcohols under Neutral Conditions

AU - Kwon, Yongseok

AU - Jung, Jaehyun

AU - Kim, Jae Hyun

AU - Kim, Woo Jung

AU - Kim, Sanghee

PY - 2017/5

Y1 - 2017/5

N2 - A mild and efficient palladium-catalyzed allylation reaction with allylic alcohols is described. The in situ activation of the allylic alcohol is achieved by using N,N-dimethylacetamide dimethyl acetal and a simple palladium catalyst (i.e., Pd(PPh3)4). The reaction system does not require acid or base additives or specially designed ligands. In addition to carbon nucleophiles, nitrogen and oxygen nucleophiles can also be used with the allylic alcohol in this transformation.

AB - A mild and efficient palladium-catalyzed allylation reaction with allylic alcohols is described. The in situ activation of the allylic alcohol is achieved by using N,N-dimethylacetamide dimethyl acetal and a simple palladium catalyst (i.e., Pd(PPh3)4). The reaction system does not require acid or base additives or specially designed ligands. In addition to carbon nucleophiles, nitrogen and oxygen nucleophiles can also be used with the allylic alcohol in this transformation.

KW - alcohols

KW - allylation

KW - amines

KW - palladium

KW - synthetic methods

UR - https://www.scopus.com/pages/publications/85013824617

U2 - 10.1002/ajoc.201600578

DO - 10.1002/ajoc.201600578

M3 - Article

AN - SCOPUS:85013824617

SN - 2193-5807

VL - 6

SP - 520

EP - 526

JO - Asian Journal of Organic Chemistry

JF - Asian Journal of Organic Chemistry

IS - 5

ER -

Amide Acetal in Palladium-Catalyzed Allylation with Allylic Alcohols under Neutral Conditions

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Keywords

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