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. Author manuscript; available in PMC: 2016 Mar 3.
Published in final edited form as: Nature. 2015 Aug 26;525(7567):87–90. doi: 10.1038/nature14885

Figure 4. Mechanistic studies support spin-center shift elimination pathway.

Figure 4

(a) Hydroxymethyl intermediate 47 can be converted to methylated 15 under net reductive conditions upon addition of formic acid-tributylamine and p-toluenesulfonic acid. (b) Deoxygenation of 47 likely proceeds via a spin-center shift pathway to cleave the alcohol C–O bond. (c) In the presence of styrene, 47 is converted to 50, presumably by trapping of radical 49.