Pd(0)-Catalyzed Carboiodination: Early Developments and Recent Advances - New Trends in Cross-Coupling: Theory and Applications - page 313

-Pd 0 L n

I

I

Pd II L n-1 I

L n-1 Pd II

+Pd 0 L n
-L

I I

I Carbopalladation,

Reductive Elimination
"Carboiodination"

-L

+Pd 0 L n

R

when L = QPhos, P t Bu 3

R

R

7.76 7.75 7.77

Productive
Intermediate

Catalytic Dead End
with Traditional Ligands

Scheme 7.36 Strategy to overcome catalyst deactivation using reversible oxidative addition.

Adapted from Ref. 110. Copyright 2013 WILEY-VCH Verlag GmbH & Co.

I

Pd(QPhos) 2 (5 mol%)
QPhos (10 mol%)
PMP (2 equiv)
PhMe, 110 °C, 6 h

I I

I

O

O

7.79 7.80

74%

Selected Examples:

I

I

I I

I

I

O

Ph

I

I

I

O

N
Me

O

I O

O O

60% 74% 76% 68% 58%

Scheme 7.37 Intramolecular carboiodination of diiodinated aromatic compounds.