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. Author manuscript; available in PMC: 2024 May 24.
Published in final edited form as: J Am Chem Soc. 2023 May 15;145(20):11005–11011. doi: 10.1021/jacs.3c03780

Table 1.

Selected Optimization of the Ni‐catalyzed Catellani annulation

graphic file with name nihms-1974541-t0006.jpg
Entrya Variations from the standard condition Yield of 3a/4/5/6 (%)b
1 None 99/0/0/1
2 w/o Ni(cod)2 0/0/0/0
3 w/o PPh2Me 2/0/7/3
4 w/o BTMG 0/0/0/0
5 other ligands instead of PPh2Me listed below
6 other base instead of BTMG listed below
7 other solvent instead of benzene listed below
8 1-chloronaphthalene instead of 1a 1/18/2/4
9 1-bromonaphthalene instead of 1a 3/31/6/6
10 1-iodonaphthalene instead of 1a 9/39/11/13
11c 5 mol% Ni(cod)2/7.5 mol% PPh2Me was used 82/0/9/4
graphic file with name nihms-1974541-t0007.jpg
a

Reaction conditions: 1a (0.1 mmol, 1.0 equiv), 2 (0.4 mmol, 4.0 equiv), Ni(cod)2 (0.01 mmol, 10 mol%), PPh2Me (0.015 mmol, 15 mol%), BTMG (0.3 mmol, 3.0 equiv), benzene (0.25 mL), 50 °C, 48 h.

b

Yields were determined by 1H NMR using CH3NO2 as an internal standard.

c

Reaction temperature was 70 °C.