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. Author manuscript; available in PMC: 2022 Apr 26.
Published in final edited form as: J Am Chem Soc. 2022 Mar 14;144(11):4764–4769. doi: 10.1021/jacs.2c00923

Table 1.

Optimization of the One-Pot Synthesis of Bicyclobutanes

graphic file with name nihms-1797163-t0007.jpg
entry base 1 (equiv) RSO2Cl (equiv) base 2 (equiv) yield (%)a
 1    n-BuLi (1) MsCl (1)   n-BuLi (1)    14
 2    Bu2Mg (1) MsCl (1)   n-BuLi (1)    32
 3    Bu2Mg (1) NsClb (1)   n-BuLi (1)    <5
 4    Bu2Mg (1) PhSO2Cl (1)   n-BuLi (1)    62
 5c    Bu2Mg (1) PhSO2Cl (1)   KOt-Bu (3)    45
 6c    Bu2Mg (1) PhSO2Cl (1)   NaH (1.2)    <5
 7    Bu2Mg (1) PhSO2Cl (1.3)   n-BuLi (1.2)  77d
a

Yield determined by 1H NMR using 1,3,5-trimethoxybenzene as internal standard.

b

NsCl: 4-O2N–C6H4SO2Cl.

c

Third stage run at 0 °C to rt.

d

Isolated yield = 77%.