A gold(i)-catalysed chemoselective three-component reaction between phenols, α-diazocarbonyl compounds and allenamides

Sifan YU; Jinzhou  Chen; Gengxin  Liu; Jinping Lei; Wenhao Hu; Huang Qiu

doi:10.1039/c9cc09470a

A gold(i)-catalysed chemoselective three-component reaction between phenols, α-diazocarbonyl compounds and allenamides

Sifan YU
, Jinzhou Chen
, Gengxin Liu
, Jinping Lei
, Wenhao Hu^*
, Huang Qiu^*

^*Corresponding author for this work

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

9 Citations (Scopus)

Abstract

Gold(I) catalysts are considered to be efficient in promoting sp2 C–H bond insertion at the para position of unprotected phenols because of the exceptionally chemical reactivity of gold-stabilized carbophilic carbocations. Herein, we present a gold(I)-catalysed three-component reaction between phenols, diazocarbonyl compounds and allenamides, affording the corresponding three-component reaction products with excellent geometric selectivity (E : Z > 20 : 1) in moderate to high yields (up to 90%) under mild conditions. Additionally, a gram-scale transformation and diverse transformations of the resulting product show the high synthetic utility of the present three-component protocol.

Original language	English
Pages (from-to)	1649-1652
Number of pages	4
Journal	Chemical Communications
Volume	56
Issue number	11
DOIs	https://doi.org/10.1039/c9cc09470a
Publication status	Published - 7 Feb 2020
Externally published	Yes

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SDG 9 Industry, Innovation, and Infrastructure

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10.1039/c9cc09470a

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title = "A gold(i)-catalysed chemoselective three-component reaction between phenols, α-diazocarbonyl compounds and allenamides",

abstract = "Gold(I) catalysts are considered to be efficient in promoting sp2 C–H bond insertion at the para position of unprotected phenols because of the exceptionally chemical reactivity of gold-stabilized carbophilic carbocations. Herein, we present a gold(I)-catalysed three-component reaction between phenols, diazocarbonyl compounds and allenamides, affording the corresponding three-component reaction products with excellent geometric selectivity (E : Z > 20 : 1) in moderate to high yields (up to 90\%) under mild conditions. Additionally, a gram-scale transformation and diverse transformations of the resulting product show the high synthetic utility of the present three-component protocol.",

author = "Sifan YU and Jinzhou Chen and Gengxin Liu and Jinping Lei 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 \& 21901262), and the Natural Science Foundation of Guangdong Province (2018A030310141). Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2020",

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doi = "10.1039/c9cc09470a",

language = "English",

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T1 - A gold(i)-catalysed chemoselective three-component reaction between phenols, α-diazocarbonyl compounds and allenamides

AU - YU, Sifan

AU - Chen, Jinzhou

AU - Liu, Gengxin

AU - Lei, Jinping

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 & 21901262), and the Natural Science Foundation of Guangdong Province (2018A030310141). Publisher Copyright: © The Royal Society of Chemistry 2020

PY - 2020/2/7

Y1 - 2020/2/7

N2 - Gold(I) catalysts are considered to be efficient in promoting sp2 C–H bond insertion at the para position of unprotected phenols because of the exceptionally chemical reactivity of gold-stabilized carbophilic carbocations. Herein, we present a gold(I)-catalysed three-component reaction between phenols, diazocarbonyl compounds and allenamides, affording the corresponding three-component reaction products with excellent geometric selectivity (E : Z > 20 : 1) in moderate to high yields (up to 90%) under mild conditions. Additionally, a gram-scale transformation and diverse transformations of the resulting product show the high synthetic utility of the present three-component protocol.

AB - Gold(I) catalysts are considered to be efficient in promoting sp2 C–H bond insertion at the para position of unprotected phenols because of the exceptionally chemical reactivity of gold-stabilized carbophilic carbocations. Herein, we present a gold(I)-catalysed three-component reaction between phenols, diazocarbonyl compounds and allenamides, affording the corresponding three-component reaction products with excellent geometric selectivity (E : Z > 20 : 1) in moderate to high yields (up to 90%) under mild conditions. Additionally, a gram-scale transformation and diverse transformations of the resulting product show the high synthetic utility of the present three-component protocol.

UR - https://pubs.rsc.org/en/content/articlelanding/2020/cc/c9cc09470a#!divAbstract

U2 - 10.1039/c9cc09470a

DO - 10.1039/c9cc09470a

M3 - Journal article

SN - 1359-7345

VL - 56

SP - 1649

EP - 1652

JO - Chemical Communications

JF - Chemical Communications

IS - 11

ER -

A gold(i)-catalysed chemoselective three-component reaction between phenols, α-diazocarbonyl compounds and allenamides

Abstract

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