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. Author manuscript; available in PMC: 2020 Feb 20.
Published in final edited form as: J Am Chem Soc. 2019 Feb 11;141(7):3083–3099. doi: 10.1021/jacs.8b12247

Scheme 9.

Scheme 9.

C–H Activation Studies of the Unactivated C13 Methyl Groupa

aReagents and conditions: (a) KOH (3.0 equiv), MeOH, 48 h, 91%; (b) [Ir(COD)(OMe)]2 (0.5 mol %), Et2SiH2 (1.5 equiv), THF, 12 h; (c) [Rh(COE)2Cl]2 (2 mol %), (S)-DTBM-SegPhos (4 mol%), norbornene (1.2 equiv), THF, 100 °C, 12 h, 25% (two steps); (d) H2O2 (50 wt% in H2O, 10.0 equiv), KHCO3 (5.0 equiv), 50 °C, 36 h, 76%; (e) NaH (1.1 equiv), ClSO2NH2 (1.5 equiv), 0 → 23 °C, 4 h, 72%; (f) Rh2(esp)2 (3 mol%), PhI(OPiv)2 (1.5 equiv), PhH, 16 h, 63%. esp = α,α,α′,α′-tetramethyl-1,3-benzenedipropionic acid.