Pd(0)-Catalyzed Carboiodination: Early Developments and Recent Advances - New Trends in Cross-Coupling: Theory and Applications - page 299

(a)

I

Pd(OAc) 2, PPh 3
Na 2 CO 3
PhMe, 90 ° C

Ph

+

PhB(OH) 2

O

O

(b)

91%

I

O

Pd(OAc) 2, PPh 3
PhMe, 90

+ Bu 3 Sn

C O

Bn °

Bn

89%

(c)

Pd(OAc) 2 , PPh 3
piperidine
MeCN, 60

O

+

H

N

N

H ONa

° C

I O

O

70%

Scheme 7.22 Extension of anion capture cascade reactions by Grigg and co-workers.

(a) Domino carbopalladation-intramolecular C − H activation

H

BnN

Pd(OAc) 2 , XPhos
K 2 CO 3
DMA, 100

O

I

BnN

° C

O O

O

7.38
90%

(b) Domino carbopalladation-intermolecular C − H activation

H

S

Pd(OAc) 2 , XPhos
PivOH, K 2 CO 3

Br

+

S

DMA, 110 ° C

Ts Ts

7.39
84%

(c) Domino carbopalladation-cyanide trapping

Pd 2 (dba) 3
Na 2 CO 3
DMF, 120

I

CN
O

O

+

K 4 [Fe(CN) 6 ]

° C

Bn N

Bn

7.40
61%

Scheme 7.23 Unique trapping of neopentylpalladium(II) intermediate.