Alkynylation of aldehydes mediated by zinc and allyl bromide: a practical synthesis of propargylic alcohols

Alkynylation of aldehydes mediated by zinc and allyl bromide: a practical synthesis of... Keywords Alkynylation  Zinc  Propargylic alcohol  a-Tertiary-hydroxy ester  a- Alkynyl alcohol Introduction Propargylic alcohols are versatile precursors for the synthesis of natural products and pharmaceutically relevant compounds [1–3]. Especially, they can be trans- formed to important carbocycles and heterocycles such as 1H-indenes [4], pyrazoles & Wen-Cai Huang hwc@scu.edu.cn Department of Pharmaceutical and Bioengineering, School of Chemical Engineering, Sichuan University, Chengdu 610065, People’s Republic of China 123 4284 J.-C. Zhou et al. [5], isoxazoles [6], tetrazoles [7], benzofurans [8] and b-lactams [9]. Different processes have been developed to prepare structurally diverse propargylic alcohols over the past decades, among which alkynylation of aldehydes is a straightforward and very useful method [10–16]. In most cases, organometallic reagents such as diethylzinc [17–21], dimethylzinc [22–24] and n-butyllithium [25, 26] are needed to abstract the active hydrogen of terminal alkynes to form metal acetylides, followed by nucleophilic addition to aldehydes to afford propargylic alcohols. However, there are some recognized limitations of this approach because these alkylmetal reagents are sensitive toward air and moisture and thus inconvenient to handle. Recently, some progress has been made in the alkynylation of aldehydes without the use of the strong bases mentioned above. ZnO, a cheap and http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Research on Chemical Intermediates Springer Journals

Alkynylation of aldehydes mediated by zinc and allyl bromide: a practical synthesis of propargylic alcohols

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Publisher
Springer Netherlands
Copyright
Copyright © 2017 by Springer Science+Business Media Dordrecht
Subject
Chemistry; Catalysis; Physical Chemistry; Inorganic Chemistry
ISSN
0922-6168
eISSN
1568-5675
D.O.I.
10.1007/s11164-016-2859-2
Publisher site
See Article on Publisher Site

Abstract

Keywords Alkynylation  Zinc  Propargylic alcohol  a-Tertiary-hydroxy ester  a- Alkynyl alcohol Introduction Propargylic alcohols are versatile precursors for the synthesis of natural products and pharmaceutically relevant compounds [1–3]. Especially, they can be trans- formed to important carbocycles and heterocycles such as 1H-indenes [4], pyrazoles & Wen-Cai Huang hwc@scu.edu.cn Department of Pharmaceutical and Bioengineering, School of Chemical Engineering, Sichuan University, Chengdu 610065, People’s Republic of China 123 4284 J.-C. Zhou et al. [5], isoxazoles [6], tetrazoles [7], benzofurans [8] and b-lactams [9]. Different processes have been developed to prepare structurally diverse propargylic alcohols over the past decades, among which alkynylation of aldehydes is a straightforward and very useful method [10–16]. In most cases, organometallic reagents such as diethylzinc [17–21], dimethylzinc [22–24] and n-butyllithium [25, 26] are needed to abstract the active hydrogen of terminal alkynes to form metal acetylides, followed by nucleophilic addition to aldehydes to afford propargylic alcohols. However, there are some recognized limitations of this approach because these alkylmetal reagents are sensitive toward air and moisture and thus inconvenient to handle. Recently, some progress has been made in the alkynylation of aldehydes without the use of the strong bases mentioned above. ZnO, a cheap and

Journal

Research on Chemical IntermediatesSpringer Journals

Published: Feb 7, 2017

References

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