Table 2 Optimization of the reaction conditions for the synthesis of 29

From: Electrochemical synthesis of allenyl silanes and allenyl boronic esters

View full size image

Entry

Deviation from standard conditions

% Yielda

1

None

56, 46b

2

Na2CO3 or NaOH instead of MeONa

46, 30

3

Graphite at both the anode and the cathode

NR

4

Platinum anode instead of SST

17

5

LiClO4 instead of Et4NBF4

23

6

CH3OH/CH3CN (4:1) instead of CH3OH

39

7

CH3OH/acetone (4:1) instead of CH3OH

42

8

rAP = 50 ms instead of 150 ms

12

9

rAP = 300 ms instead of 150 ms

39

  1. NR no reaction.
  2. aDetermined by 1HNMR yield using CH3NO2 as the internal standard. bIsolated yield.
  3. bIsolated yield.