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. Author manuscript; available in PMC: 2020 Sep 18.
Published in final edited form as: J Am Chem Soc. 2019 Sep 6;141(37):14728–14735. doi: 10.1021/jacs.9b06643

Table 5.

Secondary C(sp3)−H Arylation without Added External Ligandsa

graphic file with name nihms-1059931-t0074.jpg

entry substrate product yield, %

1 graphic file with name nihms-1059931-t0075.jpg graphic file with name nihms-1059931-t0076.jpg 68
2 graphic file with name nihms-1059931-t0077.jpg graphic file with name nihms-1059931-t0078.jpg 44
  70b
3 graphic file with name nihms-1059931-t0079.jpg graphic file with name nihms-1059931-t0080.jpg 60
4 graphic file with name nihms-1059931-t0081.jpg graphic file with name nihms-1059931-t0082.jpg 53
  79b
5c graphic file with name nihms-1059931-t0083.jpg graphic file with name nihms-1059931-t0084.jpg 82
6 graphic file with name nihms-1059931-t0085.jpg graphic file with name nihms-1059931-t0086.jpg 70
7b,d graphic file with name nihms-1059931-t0087.jpg graphic file with name nihms-1059931-t0088.jpg 75
8b,e graphic file with name nihms-1059931-t0089.jpg graphic file with name nihms-1059931-t0090.jpg 63
9b,f graphic file with name nihms-1059931-t0091.jpg graphic file with name nihms-1059931-t0092.jpg 57
a

Amide 0.5 mmol, hexafluoroisopropanol 3.5 mL. Yields are isolated yields. Please see Supporting Information for details. Ar = 4-FC6H4.

b

Ten mol % Pd(OAc)2.

c

Cis/trans 5/1.

d

Diastereomer ratio: 1.6/1; 36 h, 110 °C.

e

36 h, 110 °C.

f

Diastereomer ratio: 1.5/1; 36 h, 110 °C. PPY = 4-pyrrolidino-1-pyridyl.