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. Author manuscript; available in PMC: 2011 Oct 13.
Published in final edited form as: J Am Chem Soc. 2010 Oct 13;132(40):14137–14151. doi: 10.1021/ja105044s

Table 7.

Accelerated Pd(II)-catalyzed C–H olefination of phenylacetic acid substrates 1–10.a,b

graphic file with name nihms-238338-t0013.jpg

Product Ligand % Conv.
graphic file with name nihms-238338-t0014.jpg --- 7c
BQ 3c
Ac-Ile-OH >99 (96)
graphic file with name nihms-238338-t0015.jpg --- 25c
BQ 7c
Ac-Ile-OH 98 (97)
graphic file with name nihms-238338-t0016.jpg --- 2
BQ 1
Ac-Ile-OH >99 (98)
graphic file with name nihms-238338-t0017.jpg --- 64
BQ 9
Ac-Ile-OH 88 (83)d
graphic file with name nihms-238338-t0018.jpg --- 93 (92)
BQ 12
Ac-Ile-OH >99 (95)
graphic file with name nihms-238338-t0019.jpg --- 6
BQ 2
Ac-Ile-OH >99 (99)
graphic file with name nihms-238338-t0020.jpg --- 8e
BQ 3e
Ac-Ile-OH >99 (99)e
graphic file with name nihms-238338-t0021.jpg --- 0
BQ 0
Ac-Ile-OH 72 (70)f
graphic file with name nihms-238338-t0022.jpg --- 10
BQ 5
Ac-Ile-OH >99 (98)
graphic file with name nihms-238338-t0023.jpg --- 44g
BQ 23
Ac-Ile-OH >99 (94)
a

5 mol% BQ (when used), 10 mol% Ac-Ile-OH (when used).

b

The conversion was determined by 1H NMR analysis of the crude reaction mixture. Isolated yield is given in parentheses.

c

Average of three trials.

d

An additional 11% of the di-ortho-olefinated product was observed by 1H NMR.

e

6 h.

f

An additional 6% of the decarboxylated product was formed.

g

An additional 4% of a positional isomer was formed.