N
Me Me
Me
H
H
Bpin
Pd(OAc) 2 (10 mol%)
t-amylOH, 100 ºC, air
BQ, Ag 2 CO 3 , NaHCO 3
Ac-Phe-OH (20 mol%)
N
Me Me
Me
H
61%
1 1%
N
Me Me
Me
H
Ph
N
Me Me
Me
H
Ph
N
Me Me
Me
H
Ph
F
F
Ph
N
Me
Me
Me
H
O
N
Me Me
Me
H
Ph
N
Me Me
Me
H
O
O
F
N
Me Me
Me
H
O
O
CO 2 Et
N
Me Me
Me
H
O
O
CO 2 Me
NHBoc
61%
67%
68%
68%
50%
54%
4 5% (8%)
Scheme 3.65 Pd-catalyzed oxidative C(sp
3
)−H arylation of aliphatic amines
N
Me Me
Me
H
63%
O
O
H
N
O
O
N
71%
O
O
O
Me
Me
Me
CO 2 Et
Me
Me
Me
N
Me Me
Me
H
O
O
TIPS
H
C–H
alkynylation
81%
52%
C–H
carbonylation
C–H
alkenylation
N
O
O
O
Me
Me
Me
TIPS
N
O
O
CO 2 Et
Me
Me
Me
Si( i- Pr)3
C–H
carbonylation
C–H
alkenylation
55%
74%
Scheme 3.66 Pd-catalyzed sequential C–H functionalization of aliphatic amines