Well-Defined Ni−SNS Complex Catalysed Borrowing Hydrogenative α-Alkylation of Ketones and Dehydrogenative Synthesis of Quinolines,Advanced Synthesis & Catalysis

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Well-Defined Ni−SNS Complex Catalysed Borrowing Hydrogenative α-Alkylation of Ketones and Dehydrogenative Synthesis of Quinolines
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2022-05-22 , DOI: 10.1002/adsc.202200209
Rahul Sharma ₁ , Avijit Mondal ₁ , Arup Samanta ₁ , Nandita Biswas ₁ , Babulal Das ₁ , Dipankar Srimani ₁

Affiliation

The “borrowing hydrogen” (BH) method for C-alkylation reactions using alcohol as alkylating agents is an important synthetic transformation. In this respect, designing cheap and bench stable earth abundant metal catalyst for borrowing hydrogen transformation is a key challenge to be witnessed. Herein we have presented a synthesis of non-phosphine, easily accessible and bench stable SNS−Ni complexes. The Ni-catalyst was successfully applied for the C-alkylation of ketone enolates to α-alkylated ketones. Primary alcohol with different functional groups and various heteroaromatic alcohols are well tolerated. The present catalyst system was efficiently applied to gram scale synthesis and also the green chemistry metrics of the reaction were calculated. The present protocol was also extended successfully for the synthesis of biologically important quinoline moieties. Finally, various control experiments and deuterium labelled experiments suggest that the reaction proceeds via borrowing hydrogen pathway.

中文翻译：

定义明确的Ni-SNS配合物借用氢化α-烷基化酮和脱氢合成喹啉

使用醇作为烷基化剂的 C-烷基化反应的“借氢”（BH）方法是一种重要的合成转化。在这方面，设计用于借氢转化的廉价且台架稳定的地球丰富金属催化剂是一个需要见证的关键挑战。在这里，我们提出了一种非膦、易于获得和台架稳定的 SNS-Ni 配合物的合成。Ni催化剂成功地应用于烯醇酮的C-烷基化为α-烷基化酮。具有不同官能团的伯醇和各种杂芳醇具有良好的耐受性。本催化剂体系有效地应用于克级合成，还计算了反应的绿色化学指标。本议定书还成功地扩展了生物重要的喹啉部分的合成。最后，各种对照实验和氘标记实验表明反应是通过借氢途径进行的。

更新日期：2022-05-22

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