Facile Direct Coupling Reactions of MOM-protected Benzylic Alcohols Using Aluminum Chloride

Tien Tan Bui; Hee Kwon Kim

doi:10.1002/bkcs.12358

Facile Direct Coupling Reactions of MOM-protected Benzylic Alcohols Using Aluminum Chloride

Tien Tan Bui
, Hee Kwon Kim^*

^*Corresponding author for this work

Department of Medicine

Jeonbuk National University

Research output: Contribution to journal › Journal article › peer-review

1 Scopus citations

Abstract

MOM group is one of the most commonly used protecting groups for alcohols. This study describes novel direct functionalization of the MOM-protected benzylic alcohols. Preparation of allylic compounds from benzyl MOM ethers was successfully achieved by utilization of allyltrimethylsilane and AlCl₃. In addition, direct azidation of benzyl MOM ethers using TMSN₃ was successful carried out under AlCl₃-mediated reaction conditions. These results demonstrate that this novel synthetic procedure is a promising approach to direct functionalization of MOM-protected alcohols including allylation and azidation.

Original language	English
Pages (from-to)	1195-1198
Number of pages	4
Journal	Bulletin of the Korean Chemical Society
Volume	42
Issue number	9
DOIs	https://doi.org/10.1002/bkcs.12358
State	Published - 2021.09

Keywords

Allylation
Aluminum chloride
Azidation
Lewis acid catalysts
MOM-protected alcohols

Quacquarelli Symonds(QS) Subject Topics

Chemistry

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10.1002/bkcs.12358

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@article{db25a9d1d6e441feb65f47b43a1c58b4,

title = "Facile Direct Coupling Reactions of MOM-protected Benzylic Alcohols Using Aluminum Chloride",

abstract = "MOM group is one of the most commonly used protecting groups for alcohols. This study describes novel direct functionalization of the MOM-protected benzylic alcohols. Preparation of allylic compounds from benzyl MOM ethers was successfully achieved by utilization of allyltrimethylsilane and AlCl3. In addition, direct azidation of benzyl MOM ethers using TMSN3 was successful carried out under AlCl3-mediated reaction conditions. These results demonstrate that this novel synthetic procedure is a promising approach to direct functionalization of MOM-protected alcohols including allylation and azidation.",

keywords = "Allylation, Aluminum chloride, Azidation, Lewis acid catalysts, MOM-protected alcohols",

author = "Bui, \{Tien Tan\} and Kim, \{Hee Kwon\}",

note = "Publisher Copyright: {\textcopyright} 2021 Korean Chemical Society and Wiley-VCH GmbH.",

year = "2021",

month = sep,

doi = "10.1002/bkcs.12358",

language = "English",

volume = "42",

pages = "1195--1198",

journal = "Bulletin of the Korean Chemical Society",

issn = "0253-2964",

number = "9",

}

TY - JOUR

T1 - Facile Direct Coupling Reactions of MOM-protected Benzylic Alcohols Using Aluminum Chloride

AU - Bui, Tien Tan

AU - Kim, Hee Kwon

PY - 2021/9

Y1 - 2021/9

N2 - MOM group is one of the most commonly used protecting groups for alcohols. This study describes novel direct functionalization of the MOM-protected benzylic alcohols. Preparation of allylic compounds from benzyl MOM ethers was successfully achieved by utilization of allyltrimethylsilane and AlCl3. In addition, direct azidation of benzyl MOM ethers using TMSN3 was successful carried out under AlCl3-mediated reaction conditions. These results demonstrate that this novel synthetic procedure is a promising approach to direct functionalization of MOM-protected alcohols including allylation and azidation.

AB - MOM group is one of the most commonly used protecting groups for alcohols. This study describes novel direct functionalization of the MOM-protected benzylic alcohols. Preparation of allylic compounds from benzyl MOM ethers was successfully achieved by utilization of allyltrimethylsilane and AlCl3. In addition, direct azidation of benzyl MOM ethers using TMSN3 was successful carried out under AlCl3-mediated reaction conditions. These results demonstrate that this novel synthetic procedure is a promising approach to direct functionalization of MOM-protected alcohols including allylation and azidation.

KW - Allylation

KW - Aluminum chloride

KW - Azidation

KW - Lewis acid catalysts

KW - MOM-protected alcohols

UR - https://www.scopus.com/pages/publications/85111517439

U2 - 10.1002/bkcs.12358

DO - 10.1002/bkcs.12358

M3 - Journal article

AN - SCOPUS:85111517439

SN - 0253-2964

VL - 42

SP - 1195

EP - 1198

JO - Bulletin of the Korean Chemical Society

JF - Bulletin of the Korean Chemical Society

IS - 9

ER -

Facile Direct Coupling Reactions of MOM-protected Benzylic Alcohols Using Aluminum Chloride

Abstract

Keywords

Quacquarelli Symonds(QS) Subject Topics

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