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. 2020 Jul 14;10(44):26414–26417. doi: 10.1039/d0ra04367b

Nickel-catalyzed tandem reactions of 3-(2-hydroxy-phenyl)-acrylic acids 1 and 2-iodo-benzenethiols 2, each involving cyclic esterification/C–S bond formationa.

graphic file with name d0ra04367b-u2.jpg
Entry R R1 3 Yieldb
1 H H graphic file with name d0ra04367b-u3.jpg 83
2 5-CH3 H graphic file with name d0ra04367b-u4.jpg 84
3 5-CH3 Naphthyl graphic file with name d0ra04367b-u5.jpg 86
4 4-CH3O H graphic file with name d0ra04367b-u6.jpg 89
5 4-CH3O 4,5-diCH3O graphic file with name d0ra04367b-u7.jpg 76
6 4-CH3O Naphthyl graphic file with name d0ra04367b-u8.jpg 81
7 5-F H graphic file with name d0ra04367b-u9.jpg 71
8 5-Cl H graphic file with name d0ra04367b-u10.jpg 75
9 5-Br H graphic file with name d0ra04367b-u11.jpg 69
10 4,5-diCH3 H graphic file with name d0ra04367b-u12.jpg 74
11 4,5-diCH3O Naphthyl graphic file with name d0ra04367b-u13.jpg 72
a

Unless otherwise noted, reaction conditions were 1 (0.5 mmol), 2 (0.6 mmol), Ni(CO)4 (10 mol%), NaOEt (2 equiv.), DMSO (5 mL), 90 °C and a reaction time of 10 h.

b

Isolated yield.