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4.4.11.4 Method 4: From Bis(triorganosilyl)mercury(II) Compounds

DOI: 10.1055/sos-SD-004-00265

Singer, R. D.Science of Synthesis, (20024242.

Until the late 1970s, triorganosilyllithium reagents had been traditionally prepared from bis(triorganosilyl)mercury(II) compounds via transmetalation (metal exchange) with lithium metal, e.g. formation of silyllithium 4 (Scheme 6).[‌21‌‌23‌] The bis(triorganosilyl)mercury(II) compounds are initially prepared by the reaction of a bromo- or chlorotriorganosilane with a sodiummercury amalgam. The formation of the silyllithium species from the mercury compound with lithium metal can take days to reach completion, whereas other more popular methods afford the silyllithium adducts in a matter of hours (see Sections 4.4.11.14.4.11.3).

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