Rh(III)-Catalyzed C-H Functionalization/Annulation of 1-Arylindazolones: Divergent Synthesis of Fused Indazolones and Allyl Indazolones
Rh(III)-Catalyzed C-H Functionalization/Annulation of 1-Arylindazolones: Divergent Synthesis of Fused Indazolones and Allyl Indazolones
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DOI：
10.1021/acs.joc.2c02722
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发表时间：
2023-03-09
影响因子：
3.6
通讯作者：
Zhang，Shang-Shi
中科院分区：
文献类型：
--
作者：
Shu，Bing;Song，Jia-Lin;Zhang，Shang-Shi
以5-亚甲基-1，3-二氧杂环戊-2-酮和4-乙烯基-1，3-二氧杂环戊-2-酮为偶联配体，实现了Rh（III）催化的苯基吲唑酮的C-H/N-H成环和C-H烯丙基化反应，得到了功能化的吲唑酮稠合杂环和支链及直链烯丙基吲唑酮，产率从中等到高.这些不同的合成方案展示了温和的条件，广泛的底物范围和高官能团相容性。此外，还进行了放大合成和初步的机理探索。
Rh(III)-catalyzed C–H/N–H annulation and C–H allylation of phenylindazolones have been realized by employing 5-methylene-1,3-dioxan-2-one and 4-vinyl-1,3-dioxolan-2-one as scalable cross-coupling partners, delivering functionalized indazolone fused heterocycles and branched and linear allyl indazolones respectively in moderate to high yield. These divergent synthesis protocols showcase mild conditions, broad substrate scope, and high functional-group compatibility. In addition, scale-up synthesis and preliminary mechanistic exploratory were also accomplished.