Hydroboration—a powerful synthetic tool☆
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2021, Tetrahedron LettersCitation Excerpt :Because hydroboration is an electrophilic reaction, styrene derivatives with an electron-withdrawing group provided slightly lower yields than those with an electron-donating group. Interestingly, styrene (1c), 4-fluorostyrene (1d), and 4-chlorostyrene (1e) afforded Markovnikov alcohols 3c, 3d, and 3e in low yields (6–17%) together with anti-Markovnikov product 2c, 2d, and 2d, respectively [13]. Styrene 1e was reacted with a conventional borane reagent, BH3-THF, to afford Markovnikov alcohol 3e in a yield similar to that obtained by the PV method (Entry 5, Condition E), indicating that the regioselectivity of hydroboration under the PV conditions is hardly different from that of the conventional one [14].
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Lecture to the Organic Division at the 137th Meeting of the American Chemical Society in Cleveland, Ohio, April 12, 1960, in connection with the 1960 A.C.S. Award for Creative Work in Synthetic Organic Chemistry.