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. Author manuscript; available in PMC: 2016 Nov 20.
Published in final edited form as: J Org Chem. 2015 Oct 30;80(22):11388–11397. doi: 10.1021/acs.joc.5b01962

Table 2.

Scope of the visible-light photoredox catalyzed synthesis of 2,5-diaryl-1,5-dienes 1.

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Entry R Product (Yield in %)a
1 H (2a) 1a (81%, 80%b)
2 4-Cl (2b) 1b (80%)
3 4-Br (2c) 1c (82%)
4 3-Br (2d) 1d (84%, 79%b)
5 2-F (2e) 1e (66%)c
6 4-Me (2f) 1f (79%)d
7 3-Me (2g) 1g (85%)d
8 2-Me (2h) 1h (71%e, 69%f)
9 4-OMe (2i) 1i (59%)
10 3-OMe (2j) 1j (72%)
11 2-OMe (2k) 1k (67%)g
12 4-CN (2l) 1l (70%)
13 3-CN (2m) 1m (70%)d
a

Isolated yield of 1 after silica gel chromatography (average of two experiments).

b

1.0 mmol scale.

c

26% recovered SM 2e (89% brsm).

d

CH2Cl2 (0.2 M).

e

29% recovered SM 2h (quant. brsm).

f

1.0 mmol scale, 25% recovered SM 2h (91% brsm).

g

Ru(bpy)3(PF6)2 (1.5 mol%), 42 h reaction time, 18% recovered SM 2k (81% brsm).