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. Author manuscript; available in PMC: 2023 Aug 5.
Published in final edited form as: Science. 2022 Aug 4;377(6606):649–654. doi: 10.1126/science.abo6443

Figure 4. Mechanistic experiments.

Figure 4.

(A) This carbene reactivity is not accessible via diazoalkanes. (B) The proposed Zn carbenoid is validated by an acidic quench. Conversely, single-electron reduction affords ketyl radical reactivity, but not carbene dimerization. (C) Electrophilic character of carbene is illustrated by selective reactivity with nucleophilic traps; sulfonium ylide affords polarity-reversed reactivity with electrophiles. (D) Competition experiments illustrate catalyst role in product selectivity. (E) The improved thermal stability of these carbene precursors relative to diazoalkanes allows safer scale-up of batch chemistry.