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. Author manuscript; available in PMC: 2014 Jul 29.
Published in final edited form as: Angew Chem Int Ed Engl. 2013 Jun 18;52(31):8156–8159. doi: 10.1002/anie.201304035

Table 2.

NHC-Cu-catalyzed ECA of aryl-substituted enones with Et3AI.[a]

graphic file with name nihms-523174-t0006.jpg

Entry Ar; Substrate Product t[h] Conv. [%];[b]
Yield [%][c]
e.r.[d]
1 Ph; 2b 5a 0.5 >98; 93 98:2
2 2-thienyl; 2c 5b 1.0 >98; 86 98.5:1.5
3 pF3CC6H4; 2e 5c 1.0 >98; 89 99:1
4 pMeOC6H4; 2f 5d 1.0 >98; 92 99:1
5 2-naphthyl; 2h 5e 2.5 97; 94 97.5:2.5
6 oBrC6H4; 2i 5f 12 98; 87 >99:1
7 mFC6H4; 2j 5g 3.0 >98; 90 96.5:3.5
[a]

Reactions were performed under N2 atmosphere.

[b]

Determined through analysis of 400 MHz 1H NMR spectra of unpurified mixtures.

[c]

Yield of isolated and purified products.

[d]

Determined by GC analysis (entries 1-2) or HPLC analysis (±2%); see the Supporting Information for details.