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. 2024 Aug 6;15(35):14188–14194. doi: 10.1039/d4sc04199b

Optimization of the photocatalytic decarboxylative cyanation with isonitrilesa.

graphic file with name d4sc04199b-u1.jpg
Entry Solvent 2 (equiv.) Ir-cat (mol%) Yield 3 (3′) %
1 MeCN 2a (3.0) 2 68 (14)
2 MeCN 2b (3.0) 2 55 (35)
3 MeCN 2c (3.0) 2 30 (5)
4 MeCN 2d (3.0) 2 48 (52)
5 MeCN 2e (3.0) 2 24 (0)
6 MeCN 2f (3.0) 2 4 (12)
7 DMSO 2a (3.0) 2 74 (12)
8 DMF 2a (3.0) 2 60 (14)
9 DCM 2a (3.0) 2 0 (5)
10 PhCH3 2a (3.0) 2 36 (30)
11b,c DMSO 2a (2.5) 1 82 (8)
12d DMSO 2a (2.5) 1 0
13e DMSO 2a (2.5) 1 0
a

The reactions were performed on a 0.10 mmol scale and the yields were determined by 1H NMR with CH2Br2 as an internal standard.

b

The reaction was performed on a 0.20 mmol scale.

c

Yield determined after isolation by column chromatography purification.

d

The reaction was performed in the absence of light.

e

The reaction was performed in the absence of photocatalyst. See ESI for further details.