A gold(i)-catalysed three-component reaction via trapping oxonium ylides with allenamides

Gengxin  Liu; Sifan Yu; Wenhao Hu; Huang Qiu

doi:10.1039/C9CC06599G

A gold(i)-catalysed three-component reaction via trapping oxonium ylides with allenamides

Gengxin Liu
, Sifan Yu
, Wenhao Hu^*
, Huang Qiu^*

^*Corresponding author for this work

Chinese Medicine - Teaching and Research Division

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

13 Citations (Scopus)

Abstract

A gold(I)-catalysed three-component reaction between alcohols (and water), α-aryl-α-diazoesters and allenamides has been developed, affording three-component products, tert-allylic ethers (and alcohols), in moderate to excellent yields with excellent geometric selectivity (E : Z > 20 : 1). In addition, this transformation proceeds smoothly with high functional group tolerance and a broad substrate scope under exceptionally mild reaction conditions. Remarkably, a gram-scale reaction is also successfully performed, and the corresponding three-component product can readily react with easily obtained reagents, furnishing diverse products in satisfactory yields.

Original language	English
Pages (from-to)	12675-12678
Number of pages	4
Journal	Chemical Communications
Volume	55
Issue number	84
DOIs	https://doi.org/10.1039/C9CC06599G
Publication status	Published - 28 Oct 2019

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title = "A gold(i)-catalysed three-component reaction via trapping oxonium ylides with allenamides",

abstract = "A gold(I)-catalysed three-component reaction between alcohols (and water), α-aryl-α-diazoesters and allenamides has been developed, affording three-component products, tert-allylic ethers (and alcohols), in moderate to excellent yields with excellent geometric selectivity (E : Z > 20 : 1). In addition, this transformation proceeds smoothly with high functional group tolerance and a broad substrate scope under exceptionally mild reaction conditions. Remarkably, a gram-scale reaction is also successfully performed, and the corresponding three-component product can readily react with easily obtained reagents, furnishing diverse products in satisfactory yields.",

author = "Gengxin Liu and Sifan Yu and Wenhao Hu and Huang Qiu",

note = "We acknowledge the financial support from the Guangdong Innovative and Entrepreneurial Research Team Program (No. 2016ZT06Y337), the National Natural Science Foundation of China (21801255), and the Natural Science Foundation of Guangdong Province (2018A030310141). Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2019",

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doi = "10.1039/C9CC06599G",

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T1 - A gold(i)-catalysed three-component reaction via trapping oxonium ylides with allenamides

AU - Liu, Gengxin

AU - Yu, Sifan

AU - Hu, Wenhao

AU - Qiu, Huang

N1 - We acknowledge the financial support from the Guangdong Innovative and Entrepreneurial Research Team Program (No. 2016ZT06Y337), the National Natural Science Foundation of China (21801255), and the Natural Science Foundation of Guangdong Province (2018A030310141). Publisher Copyright: © The Royal Society of Chemistry 2019

PY - 2019/10/28

Y1 - 2019/10/28

N2 - A gold(I)-catalysed three-component reaction between alcohols (and water), α-aryl-α-diazoesters and allenamides has been developed, affording three-component products, tert-allylic ethers (and alcohols), in moderate to excellent yields with excellent geometric selectivity (E : Z > 20 : 1). In addition, this transformation proceeds smoothly with high functional group tolerance and a broad substrate scope under exceptionally mild reaction conditions. Remarkably, a gram-scale reaction is also successfully performed, and the corresponding three-component product can readily react with easily obtained reagents, furnishing diverse products in satisfactory yields.

AB - A gold(I)-catalysed three-component reaction between alcohols (and water), α-aryl-α-diazoesters and allenamides has been developed, affording three-component products, tert-allylic ethers (and alcohols), in moderate to excellent yields with excellent geometric selectivity (E : Z > 20 : 1). In addition, this transformation proceeds smoothly with high functional group tolerance and a broad substrate scope under exceptionally mild reaction conditions. Remarkably, a gram-scale reaction is also successfully performed, and the corresponding three-component product can readily react with easily obtained reagents, furnishing diverse products in satisfactory yields.

UR - https://pubs.rsc.org/en/content/articlelanding/2019/cc/c9cc06599g

U2 - 10.1039/C9CC06599G

DO - 10.1039/C9CC06599G

M3 - Journal article

SN - 1359-7345

VL - 55

SP - 12675

EP - 12678

JO - Chemical Communications

JF - Chemical Communications

IS - 84

ER -

A gold(i)-catalysed three-component reaction via trapping oxonium ylides with allenamides

Abstract

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