2.2 Arylation via a Smiles rearrangement
23
Figure 24: X-ray structure of Smiles product 2.3b. (Adapted from Gonçalves et al. 2019,
https://pubs.acs.org/doi/10.1021/jacs.9b06956; with kind permission from ©
ACS Publications 2020. All Rights Reserved)
The thought of combining the -amination and the rearrangement event in a
single step was appealing. Despite the moderate yield in the optimisation of the
Smiles rearrangement, a few one-pot experiments were carried out. Their results
are summarised in Table 3. Entries 2 and 3 were the only cases in which Smiles
product 2.3a was obtained. Huge excess of Pr4NOH as well as the absence of DMF
seemed to be crucial.
23
Figure 24: X-ray structure of Smiles product 2.3b. (Adapted from Gonçalves et al. 2019,
https://pubs.acs.org/doi/10.1021/jacs.9b06956; with kind permission from ©
ACS Publications 2020. All Rights Reserved)
The thought of combining the -amination and the rearrangement event in a
single step was appealing. Despite the moderate yield in the optimisation of the
Smiles rearrangement, a few one-pot experiments were carried out. Their results
are summarised in Table 3. Entries 2 and 3 were the only cases in which Smiles
product 2.3a was obtained. Huge excess of Pr4NOH as well as the absence of DMF
seemed to be crucial.