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. Author manuscript; available in PMC: 2024 Apr 5.
Published in final edited form as: J Am Chem Soc. 2023 Mar 23;145(13):7278–7287. doi: 10.1021/jacs.2c13146

Table 2.

Development of a Petasis borono–Mannich coupling between boronic acids and hydroxy-indoles.

graphic file with name nihms-1903612-t0003.jpg
Entry Conditions Yield of 39a
1 MeOH, CH2Cl2, or CH3CN –
2 TFE 16%b
3 HFIP 79%, 9:1 d.r. (64% isolated)
4 i-PrOH –
5 1 equiv ArB(OH)2, HFIP 31% b
6 60 °C, HFIP 72% b
7 ArBpin, HFIP <5% b
8 ArBF3K, HFIP 34% b
a

Yields determined by 1H NMR analysis of crude reaction mixture relative to Et4Si internal standard.

b

Diastereomeric ratio not determined.