期刊
NATURE COMMUNICATIONS
卷 12, 期 1, 页码 -出版社
NATURE PORTFOLIO
DOI: 10.1038/s41467-021-24027-6
关键词
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资金
- National Key Research and Development Program of China [2019YFE0109200]
- NSFC [U1702286]
- Program for Changjiang Scholars and Innovative Research Teams in Universities [IRT17R94]
- China Postdoctoral Science Foundation [2019M663581]
- NSF of Yunnan Province [2019FY003010, 202005AB160003]
- YunLing Scholar Programs
- IRTSTYN
- US National Science Foundation [CHE-1902509]
In this study, a transition-metal-free allylation strategy with allyl ether electrophiles is demonstrated to form homoallylic amine derivatives in up to 92% yield, providing valuable insights into C(sp(3))-C(sp(3)) bond-forming reactions.
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(sp(3))-C(sp(3)) bond-forming reactions. Allylation of nucleophiles with less reactive electrophiles, such as carbonates, usually requires a transition-metal catalyst. Here, the authors show a transition-metal-free allylation strategy with allyl ether electrophiles to form homoallylic amine derivatives in up to 92% yield.
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