Transition-metal-free allylation of 2-azaallyls with allyl ethers through polar and radical mechanisms

Guogang Deng, Shengzu Duan, Jing Wang, Zhuo Chen, Tongqi Liu, Wen Chen, Hongbin Zhang (), Xiaodong Yang () and Patrick J. Walsh ()
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Guogang Deng: School of Chemical Science and Technology, Yunnan University
Shengzu Duan: School of Chemical Science and Technology, Yunnan University
Jing Wang: School of Chemical Science and Technology, Yunnan University
Zhuo Chen: School of Chemical Science and Technology, Yunnan University
Tongqi Liu: School of Chemical Science and Technology, Yunnan University
Wen Chen: School of Chemical Science and Technology, Yunnan University
Hongbin Zhang: School of Chemical Science and Technology, Yunnan University
Xiaodong Yang: School of Chemical Science and Technology, Yunnan University
Patrick J. Walsh: University of Pennsylvania

Nature Communications, 2021, vol. 12, issue 1, 1-11

Abstract: Abstract Allylation of nucleophiles with highly reactive electrophiles like allyl halides can be conducted without metal catalysts. Less reactive electrophiles, such as allyl esters and carbonates, usually require a transition metal catalyst to facilitate the allylation. Herein, we report a unique transition-metal-free allylation strategy with allyl ether electrophiles. Reaction of a host of allyl ethers with 2-azaallyl anions delivers valuable homoallylic amine derivatives (up to 92%), which are significant in the pharmaceutical industry. Interestingly, no deprotonative isomerization or cyclization of the products were observed. The potential synthetic utility and ease of operation is demonstrated by a gram scale telescoped preparation of a homoallylic amine. In addition, mechanistic studies provide insight into these C(sp3)–C(sp3) bond-forming reactions.

Date: 2021
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DOI: 10.1038/s41467-021-24027-6

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