Potassium Alkylpentafluorosilicates, Primary Alkyl Radical Precursors in the C-1 Alkylation of Tetrahydroisoquinolines,Organic Letters

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Potassium Alkylpentafluorosilicates, Primary Alkyl Radical Precursors in the C-1 Alkylation of Tetrahydroisoquinolines
Organic Letters ( IF 4.9 ) Pub Date : 2019-05-13 00:00:00 , DOI: 10.1021/acs.orglett.9b01124
Teng Wang ₁ , Dong-Hui Wang ₁

Affiliation

In this study, we demonstrate that potassium alkylpentafluorosilicates (RSiF₅K₂) are efficient primary alkyl radical precursors for selective C(sp³)–C(sp³) bond-forming reactions. RSiF₅K₂ reagents are white, free-flowing solids and are moisture and air stable. This class of reagents enables the direct C-1 alkylation of tetrahydroisoquinolines under mild conditions via single-electron transfer. The broad substrate scope of both alkylpentafluorosilicates and tetrahydroisoquinolines is tolerated in this transformation. Both radical scavenger and EPR capture experiments show that the primary radical is generated by the oxidation of RSiF₅K₂. A mechanism involving alkyl radical addition to an iminium salt followed by reduction by an amine is proposed.

中文翻译：

烷基铝氟硅酸钾，四氢异喹啉C-1烷基化中的主要烷基自由基前体

在这项研究中，我们证明了烷基五氟硅酸钾（RSiF ₅ K ₂）是选择性C（sp ³）–C（sp ³）键形成反应的有效伯烷基自由基前体。RSiF ₅ K ₂试剂是白色的，可自由流动的固体，对湿气和空气稳定。这类试剂可在温和条件下通过单电子转移将四氢异喹啉直接C-1烷基化。在该转化中，烷基五氟硅酸盐和四氢异喹啉都具有宽泛的底物范围。自由基清除剂和EPR捕获实验均表明，主要自由基是由RSiF ₅ K ₂的氧化产生的。提出了一种机制，该机制涉及将烷基自由基加到亚胺盐中，然后用胺还原。

更新日期：2019-05-13

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