Allyl-Nickel Catalysis Enables Carbonyl Dehydrogenation and Oxidative Cycloalkenylation of Ketones

Allyl-Nickel Catalysis Enables Carbonyl Dehydrogenation and Oxidative Cycloalkenylation of Ketones
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DOI:
10.1021/jacs.9b02552
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发表时间:
2019-04-10
影响因子:
15
通讯作者:
Newhouse, Timothy R.
Newhouse, Timothy R.
中科院分区:
化学1区
文献类型:
--
作者:
Huang, David;Szewczyk, Suzanne M.;Newhouse, Timothy R.

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我们在此公开了使用烯丙基镍催化的第一行过渡金属催化的羰基化合物的α,β-脱氢的首次报道。这种发展克服了先前报道的烯丙基钯催化氧化的几个限制,并且进一步用于开发氧化性环烯基化反应,该反应使用未活化的酮和烯烃前体提供获得具有稠合、桥接和螺环系统的双环烯酮的途径。
We herein disclose the first report of a first-row transition metal-catalyzed alpha,beta-dehydrogenation of carbonyl compounds using allyl-nickel catalysis. This development overcomes several limitations of previously reported allyl-palladium-catalyzed oxidation, and is further leveraged for the development of an oxidative cycloalkenylation reaction that provides access to bicycloalkenones with fused, bridged, and spirocyclic ring systems using unactivated ketone and alkene precursors.