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. Author manuscript; available in PMC: 2018 Dec 13.
Published in final edited form as: J Am Chem Soc. 2017 Nov 27;139(49):18107–18114. doi: 10.1021/jacs.7b11197

Table 4.

Hindered Phenolsa

graphic file with name nihms926561u5.jpg
Entry Phenol 3% Remainingb 4% Yieldb,c 6% Yieldb,c erd
1 graphic file with name nihms926561t10.jpg 5 4k, 67 (50) 6k, 14 (9) 97:3
2 graphic file with name nihms926561t11.jpg 7 4l, 60 (43) 6l, 15 (14) 97:3
3 graphic file with name nihms926561t12.jpg 7 4m, 53 (43) 6m, 13 (8) 99:1
4 graphic file with name nihms926561t13.jpg 3 4n, 33 (33) 6n, 14 (6) 97:3
5 graphic file with name nihms926561t14.jpg 4 4o, 18 (10) 6o, 0 96:4
a

Reported results are the average of two trials. Reaction conditions: 3 (0.2 mmol), phenol (1.3 equiv), Cu(MeCN)4BF4 (10 mol %), peptide (20 mol %), K3PO4 (4.0 equiv.) and MeCN (0.8 mL), 60 °C.

b

Yield was determined using 1H NMR by comparing to an internal NMR standard (1,4-bis(trimethylsilyl)benzene).

c

The numbers in parentheses are isolated yields.

d

Enantiomeric ratios were determined using chiral HPLC analysis.