Journal of Organic Chemistry p. 5903 - 5914 (2016)
Update date:2022-07-31
Topics:
McDonald, Chriss E.
Ramsey, Jeremy D.
McAtee, Christopher C.
Mauck, Joseph R.
Hale, Erin M.
Cumens, Justin A.
A novel mode of SmI2 activation has been developed using ureates as reaction promoters. Several ureates formed by treatment of the corresponding ureas with n-BuLi have been shown to activate SmI2 to a substantial extent toward the reduction of 1-chlorodecane. Complexes formed from SmI2 and various ureates have been shown to be useful for the reduction of a variety of organohalides, including substrates of low reactivity such as aryl fluorides. Because of ease of synthesis and low molecular weight, the conjugate base of triethylurea (TEU-) was of primary focus. Visible spectroscopy and reactivity data are consistent with the hypothesis that the same complex is being formed when SmI2 is combined with either 2 or 4 equiv of TEU-, in spite of the greater reactivity of SmI2/4 TEU- with some alkyl halides. We propose that the active reductant is an N,O chelate formed between SmI2 and 2 equiv of TEU-.
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