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. Author manuscript; available in PMC: 2017 Oct 4.
Published in final edited form as: Angew Chem Int Ed Engl. 2016 Jun 22;55(41):12596–12624. doi: 10.1002/anie.201600547

Table 3.

Tetrabutylammonium-Templated Norrish-Yang Cyclization.

Entry Substrate[a] X = Solvent NBu4F (equiv) Conv.[b] (%) d.r. (55: 56)
1 54a H PhCF3 0 17 [c] 0:100 [c]
2 5 93 [c] 93:7 [c]

3 MeCN 0 35 [c] 17:83 [c]
4 5 96 [c] 84:16 [c]

5 54b Me MeCN 0 35 20:80
6 5 84 93:7

7 54c OMe MeCN 0 70 11:89
8 5 99 94:6

9 54d CF3 MeCN 0 33 23:77
10 5 6 59:41
[a]

See the substrate structure and substitution pattern in Scheme 16.

[b]

Conversion of 54 after 24 hours.

[c]

After 10 hours.