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. Author manuscript; available in PMC: 2018 Apr 26.
Published in final edited form as: J Am Chem Soc. 2017 Apr 13;139(16):5724–5727. doi: 10.1021/jacs.7b02196

Scheme 2.

Scheme 2

Diversifiations of Brominated Productsa

a Conditions: (a) NaCN (2.0 equiv), THP (tetrahydropyran), 80 °C, 24 h; (b) NaN3 (4.0 equiv), MeOH, 40 °C, 24 h; (c) pyrrolidine (2.0 equiv), K2CO3 (1.5 equiv), THF, r.t., 1 h; (d) Bn2NH (2.0 equiv), K2CO3 (1.5 equiv), THF, 80 °C, 24 h; (e) AgNO3 (2.0 equiv), EtOAc, 80 °C, 24 h; (f) PhSH (2.0 equiv), NaOH (2.0 equiv), EtOH, 40 °C, 1 h; (g) NaCN (2.0 equiv), THF, 80 °C, 24 h; (h) morpholine (2.0 equiv), K2CO3 (1.5 equiv), THF, r.t., 1 h.