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6.1.38.1.1 Variation 1: With Borane Complexes

DOI: 10.1055/sos-SD-006-00903

Zaidlewicz, M.; Krzeminski, M.Science of Synthesis, (200561104.

Early hydroboration procedures utilized diborane generated in situ and usually in diglyme solution.[‌1‌] Later, externally generated diborane was introduced into a solution of an alkene in diethyl ether or tetrahydrofuran. Although diborane is only sparingly soluble in diethyl ether at room temperature, a low concentration of the reactive boranediethyl ether complex in equilibrium with diborane is sufficient for effective hydroboration. Stronger complexation of borane by tetrahydrofuran makes possible the preparation of 12M solutions of borane by absorbing diborane in tetrahydrofuran, and a 1.0M solution is commercially available. Diborane is conveniently generated by the reaction of sodium borohydride with boron trifluoridediethyl ether complex in diglyme (Scheme 17).[‌1‌]

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Meeee Meeeeeee [MM8] Meeeeeeeeeeee Meee (eee) Mee
MeMMe(eMe) 8.8 88 [‌88‌,‌88‌,‌88‌]
MeMMe(eMe) 8.8 88 [‌88‌]
eMe8M(eMe) 8.8 88 [‌88‌,‌88‌]
e-MeMMeeMe 8.8 88 [‌88‌]
e-MeMMe(eMe) 8.8 88 [‌88‌]
e-MeM(MM8MM8MMe)8 8.8 88 [‌88‌]
Me8M[MMe8MM8e-Me] 8.8 88 [‌88‌]

Meeeeeeeeeee Meeeeeeee

Mee-eee-eeeeeeeeeee (8, M8=M8=Me; M8=M); Meeeeee Meeeeeeee:[‌8‌]

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Meeeeeeeeeeeee [8, M8=(MM8)8Me; M8=M8=M]; Meeeeee Meeeeeeee:[‌8‌]

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References


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