Rh(III)-Catalyzed Annulation of 2-Biphenylboronic Acid with Diverse Activated Alkenes,Organic Letters

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Rh(III)-Catalyzed Annulation of 2-Biphenylboronic Acid with Diverse Activated Alkenes
Organic Letters ( IF 4.9 ) Pub Date : 2021-09-01 , DOI: 10.1021/acs.orglett.1c02597
Bingxian Liu ₁ , Lingyun Yang ₁ , Zhenzhen Dong ₁ , Junbiao Chang ₁ , Xingwei Li _{1,

2}

Affiliation

Rhodium(III)-catalyzed annulation of 2-biphenylboronic acids with three classes of activated alkenes has been realized, leading to the synthesis of fused or bridged cyclic skeletons via transmetalation-initiated C–H activation. In the annulative coupling of 2-biphenylboronic acid with a CF₃-substituted enone, the bulky cyclopentadienyl ligand (Cp^tBu) in the catalyst proved effective to promote the reductive elimination process prior to protonolysis, affording the [4 + 2] annulated products instead of the simple 1,4-addition product. Seven-membered rings were obtained when disubstituted cyclopropenones were employed. Bridged cycles were isolated from the coupling of 2-biphenylboronic acid with benzoquinones as a result of 2-fold Michael additions. The substrate scopes were found to be broad with up to 99% yield under air-tolerant conditions.

中文翻译：

Rh(III)-催化 2-联苯硼酸与多种活性烯烃的环化

已经实现了铑（III）催化的 2-联苯硼酸与三类活化烯烃的环化，通过金属转移引发的 C-H 活化合成稠合或桥连的环状骨架。在 2-联苯硼酸与 CF ₃取代的烯酮的环状偶联中，庞大的环戊二烯基配体 (Cp ^{t Bu}) 在催化剂中被证明有效地促进质子分解之前的还原消除过程，提供 [4 + 2] 环化产物而不是简单的 1,4-加成产物。当使用双取代的环丙烯酮时，得到七元环。由于 2 倍迈克尔加成，从 2-联苯硼酸与苯醌的偶联中分离出桥接环。发现底物范围很广，在耐气条件下的产率高达 99%。

更新日期：2021-09-17

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