Fig. 3. Substrate scope for the electrocatalytic alkene diazidation.
All yields are of isolated products. (A) Alkene substitution patterns and
electronic properties. (B) Functional group compatibility. (C) Reduction of
diazide to diamine. *Unless otherwise noted, reaction conditions were
as follows: 0.2 mmol alkene, 0.01 mmol MnBr2·4H2O, 1.0 mmol NaN3,
400 ml of HOAc, 3.5 ml of LiClO4 solution in MeCN (0.1 M, 1.75 equiv
LiClO4), RVC as the anode, Pt as the cathode, under N2, at 22 ± 1°C, in a
one-compartment cell, at 2.3 V cell potential, for 2 to 6 hours. †Yield
of reaction is reported on a 3-mmol scale. ‡With 0.6 mmol NaN3.
§With TBAPF6 instead of LiClO4. ||With 10 mol% MnBr2·4H2O.
¶With 300 ml of HOAc. #Reaction at 40°C. **See the supplementary
materials for detailed reaction conditions. ††Yield of product is reported
with respect to alkene a. dr, diastereomeric ratio; OBn, benzyloxy; Ts,
p-toluenesulfonyl; Et, ethyl.