Chemoselective Claisen-Schmidt bis-substitutional condensation catalyzed by an alkoxy-bridged dinuclear Ti(IV) cluster

Yufei Wu; Jie Hou; Yuliang Liu; Mingfu Zhang; Chen Ho Tung; Yifeng Wang

doi:10.1016/j.tet.2016.01.055

Chemoselective Claisen-Schmidt bis-substitutional condensation catalyzed by an alkoxy-bridged dinuclear Ti(IV) cluster

Yufei Wu, Jie Hou, Yuliang Liu, Mingfu Zhang, Chen Ho Tung, Yifeng Wang

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

9 Scopus citations

Abstract

The highly efficient and chemoselective α,α′-bis-substitution of alkanones is important in organic synthesis. Herein, a dimeric titanium cluster, Ti₂Cl₂(OPrⁱ)₆·2HOPrⁱ (Ti₂), is used in the Claisen-Schmidt condensation reaction, for the selectively activation of symmetrical ketones containing α,α′-methylene groups and production of α,α′-bis-substituted alkanones in high efficiency and chemoselectivity. The high efficiency and chemoselectivity can be extended to a variety of typical alkanones and aromatic aldehydes. Both of the oxo-bridged dimeric motif of Ti₂ and the ionic Ti-Cl bond are responsible for the high efficiency and chemoselectivity.

Original language	English
Pages (from-to)	1511-1516
Number of pages	6
Journal	Tetrahedron
Volume	72
Issue number	12
DOIs	https://doi.org/10.1016/j.tet.2016.01.055
State	Published - 24 Mar 2016
Externally published	Yes

Keywords

Bis substitution
Bis-substituted alkanone
Claisen-Schmidt reaction
Crossed-aldol reaction
Dinuclear cluster

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2016.01.055

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title = "Chemoselective Claisen-Schmidt bis-substitutional condensation catalyzed by an alkoxy-bridged dinuclear Ti(IV) cluster",

abstract = "The highly efficient and chemoselective α,α′-bis-substitution of alkanones is important in organic synthesis. Herein, a dimeric titanium cluster, Ti2Cl2(OPri)6·2HOPri (Ti2), is used in the Claisen-Schmidt condensation reaction, for the selectively activation of symmetrical ketones containing α,α′-methylene groups and production of α,α′-bis-substituted alkanones in high efficiency and chemoselectivity. The high efficiency and chemoselectivity can be extended to a variety of typical alkanones and aromatic aldehydes. Both of the oxo-bridged dimeric motif of Ti2 and the ionic Ti-Cl bond are responsible for the high efficiency and chemoselectivity.",

keywords = "Bis substitution, Bis-substituted alkanone, Claisen-Schmidt reaction, Crossed-aldol reaction, Dinuclear cluster",

author = "Yufei Wu and Jie Hou and Yuliang Liu and Mingfu Zhang and Tung, {Chen Ho} and Yifeng Wang",

year = "2016",

month = mar,

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doi = "10.1016/j.tet.2016.01.055",

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T1 - Chemoselective Claisen-Schmidt bis-substitutional condensation catalyzed by an alkoxy-bridged dinuclear Ti(IV) cluster

AU - Wu, Yufei

AU - Hou, Jie

AU - Liu, Yuliang

AU - Zhang, Mingfu

AU - Tung, Chen Ho

AU - Wang, Yifeng

PY - 2016/3/24

Y1 - 2016/3/24

N2 - The highly efficient and chemoselective α,α′-bis-substitution of alkanones is important in organic synthesis. Herein, a dimeric titanium cluster, Ti2Cl2(OPri)6·2HOPri (Ti2), is used in the Claisen-Schmidt condensation reaction, for the selectively activation of symmetrical ketones containing α,α′-methylene groups and production of α,α′-bis-substituted alkanones in high efficiency and chemoselectivity. The high efficiency and chemoselectivity can be extended to a variety of typical alkanones and aromatic aldehydes. Both of the oxo-bridged dimeric motif of Ti2 and the ionic Ti-Cl bond are responsible for the high efficiency and chemoselectivity.

AB - The highly efficient and chemoselective α,α′-bis-substitution of alkanones is important in organic synthesis. Herein, a dimeric titanium cluster, Ti2Cl2(OPri)6·2HOPri (Ti2), is used in the Claisen-Schmidt condensation reaction, for the selectively activation of symmetrical ketones containing α,α′-methylene groups and production of α,α′-bis-substituted alkanones in high efficiency and chemoselectivity. The high efficiency and chemoselectivity can be extended to a variety of typical alkanones and aromatic aldehydes. Both of the oxo-bridged dimeric motif of Ti2 and the ionic Ti-Cl bond are responsible for the high efficiency and chemoselectivity.

KW - Bis substitution

KW - Bis-substituted alkanone

KW - Claisen-Schmidt reaction

KW - Crossed-aldol reaction

KW - Dinuclear cluster

UR - http://www.scopus.com/inward/record.url?scp=84958917252&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2016.01.055

DO - 10.1016/j.tet.2016.01.055

M3 - Article

AN - SCOPUS:84958917252

SN - 0040-4020

VL - 72

SP - 1511

EP - 1516

JO - Tetrahedron

JF - Tetrahedron

IS - 12

ER -

Chemoselective Claisen-Schmidt bis-substitutional condensation catalyzed by an alkoxy-bridged dinuclear Ti(IV) cluster

Abstract

Keywords

ASJC Scopus subject areas

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