Synthesis of Multisubstituted Allenes via Nickel-Catalyzed Cross-Electrophile Coupling,ACS Catalysis

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Synthesis of Multisubstituted Allenes via Nickel-Catalyzed Cross-Electrophile Coupling
ACS Catalysis ( IF 11.3 ) Pub Date : 2021-10-19 , DOI: 10.1021/acscatal.1c04143
Youxiang Jin ₁ , Hao Wen ₁ , Feiyan Yang ₁ , Decai Ding ₁ , Chuan Wang _{1,

2}

Affiliation

In this context, we report the successful application of a cross-electrophile strategy in the synthesis of multisubstituted allenes. Under the catalysis of nickel, reductive cross-coupling between propargyl carbonates and organoiodides provides an entry to prepare tri- or tetrasubstituted allenes without employing any pregenerated organometallics. Furthermore, propargyl carbonates also prove to be suitable allenylating agents in nickel-catalyzed asymmetric reductive aryl-allenylation of aryl-iodide-tethered unactivated alkenes, furnishing a variety of chiral benzene-fused cyclic compounds bearing a quaternary allenyl-substituted stereogenic center in a highly enantioselective manner.

中文翻译：

通过镍催化交叉电化学偶联合成多取代的艾伦烯

在这种情况下，我们报告了交叉亲电策略在多取代丙二烯合成中的成功应用。在镍的催化下，炔丙基碳酸酯和有机碘化物之间的还原性交叉偶联为制备三或四取代的丙二烯提供了一种途径，而无需使用任何预生成的有机金属化合物。此外，碳酸炔丙酯也被证明是合适的烯丙基化剂，用于镍催化的芳基碘系未活化烯烃的不对称还原芳基烯基化，提供各种手性苯稠合环状化合物，这些化合物在高度对映选择性方式。

更新日期：2021-11-05

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