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. 2023 Jun 22;88(13):9130–9135. doi: 10.1021/acs.joc.3c00761

Table 2. Yield and Regioselectivity of Thallium(I) Dihydrobis(pyrazolyl)borate Complexes (2afTl)a.

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Pyrazole R3 R4 R5 BpxTl (2Tl) Yield (%)b
1a tBu H H 90
1b tBu Br H 87
1c tBu NO2 H 92
1f Ms Br H 76c
a

Reaction conditions: 1ac (10.1 mmol), NaH (10.1 mmol), toluene (50 mL) 30 min at 0 °C, BH2Cl·SMe2 (5 mmol) 24 h at rt. Evaporation and addition of THF (30 mL), TlOAc (7.5 mmol), 2 h at rt.

b

Isolated yield.

c

20.1 mmol of 1f and NaH (4.02 equiv) were used.