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. Author manuscript; available in PMC: 2021 Apr 15.
Published in final edited form as: J Am Chem Soc. 2020 Sep 11;142(38):16493–16505. doi: 10.1021/jacs.0c08599

Figure 11. Structure Determination of Products.

Figure 11.

(a) Under the standard reaction conditions for installation of the alkyne unit, no intra- and/or intermolecular H/D exchange was observed between N–CD3 and N–CH2Ph groups, indicating that in situ generated iminium salt is rapidly consumed through C–alkynyl bond forming reaction vs H/D scrambling. (b) Spectroscopic studies (1H and 2H NMR) involving pure compounds revealed that Ph3C–D and Me3Si–O–SiMe3 are the stable byproducts. See the Supporting Information for details.