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. Author manuscript; available in PMC: 2011 Jun 23.
Published in final edited form as: J Am Chem Soc. 2010 Jun 23;132(24):8270–8272. doi: 10.1021/ja1033167

Table 1.

Optimization of ortho-Acetoxylation Reaction Conditions

graphic file with name nihms-210250-t0003.jpg

entry substrate additive (equiv) solvent T, °C yield, %a
1 A none PrCN 80 -b
2 B none PrCN 80 -b
3 1a none PrCN 80 15 (2a)b
4 1a none PrCN 100 30 (2a)b
5 1a Cu(OAc)2 (1) PrCN 100 trace (2a)
6 1a AgOAc (1) PrCN 80 70 (2a)
7 1a AgOAc (1) PrCN 100 80 (2a)
8 1a AgOAc (1) DCE 80 85 (2a)
a

NMR yield.

b

Decomposition of starting arylsilane was observed.