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letter
. 2017 May 15;13:903–909. doi: 10.3762/bjoc.13.91

Table 4.

Reaction scope of the visible light-mediated coupling of arenediazonium tetrafluoroborates 1 with CS2 (2).

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Substrate 1a Product 3, yieldb Substrate 1a Product 3, yieldb

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1a
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3a, 80%, 50%c
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1i
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3i, 94%, 82%c
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1b
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3b, 81%, 78%c
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1j
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3j, 99%, 85%c
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1c
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3c, 85%, 72%c
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1k
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3k, 70%
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1d
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3d, 94%
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1l
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3l, 76%
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1e
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3e, 90%
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1m
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3m, 56%
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1f
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3f, 88%
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1n
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3n, 42%
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1g
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3g, 88%
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1o
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3o, 56%
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1h
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3h, 76%
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1p
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3p, 90%c, 92%c,d

aReaction conditions: 1 (0.1 mmol), CS2 (0.2 mmol), Ru(bpy)3(PF6)2 (0.001 mmol), blue light (20 W), DMSO (2 mL), rt, 6 h; bisolated yields after chromatography on silica gel; cthe reactions were carried out with the diazonium salts 1 at a 5 mmol scale; dacetone was used as the solvent.