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. 2020 Nov 27;12(4):1544–1550. doi: 10.1039/d0sc05543c

Optimization of reaction conditionsa,b.

graphic file with name d0sc05543c-u1.jpg
Entry Deviation from the standard conditions Yieldc,d [%]
1 None 75
2 5% aq. xylene/120 °C instead of H2O/100 °C 56e
3 CH3CN/80 °C instead of H2O/100 °C 21
4 THF/70 °C instead of H2O/100 °C 32
5 1,4-Dioxane/100 °C instead of H2O/100 °C 25
6 t-BuOH/85 °C instead of H2O/100 °C 31
7 80 °C instead of 100 °C 48
8 Rh(COD)2OTf/xylene instead of [Rh(COD)CI]2 catalyst/H2O 16
9 Rh(COD)2SbF6/xylene instead of [Rh(COD)CI]2 catalyst/H2O 25
10 [Ir(COD)CI]2/xylene instead of [Rh(COD)CI]2 catalyst/H2O 21
11 [Ru(p-cymene)CI2]2/xylene instead of [Rh(COD)CI]2 catalyst/H2O 12
a

Reaction conditions: 1a (0.3 mmol) and catalyst (5 mol%) in 3 mL of solvent under an inert atmosphere.

b

All commercial solvents used in the reaction.

c

Isolated yields of exo-2a.

d

Observed exclusive exo-selectivity.

e

46% yield observed in the presence of commercial xylene.