Ph
O
O
F
N
SO
2 Ph
SO
2 Ph
9
Carbene
formation
via TS15
Nucleophilic
attack
via TS16
Ph
O
[Rh]
Ph
O
[Rh]
O
Electrophilic
fluorination
via TS17
Nucleophilic
attack
via TS18
TS17
F
Ph
O
N
2
[Rh]
3
Int14
Int15
Int16
(Rh-carbene)
Int17
(onium ylide)
Int18
(Rh-enolate)
Int19
F
13
N
2
14
O
[Rh]
13
Ph
O
O
[Rh]
SO
2 Ph
PhO
2 S
F
N
Ph
O
O
[Rh]
N
F
PhO
2 S SO
2 Ph
Ph
O
O
[Rh]
N
F
SO
2 Ph
SO
2 Ph
Ph
O
O
F
N
SO
2 Ph
SO
2 Ph
[Rh]
Int20
F
Coordination
change
Ph
O
N
2
[Rh]
Ph
O
[Rh]
O
Ph
O
O C
[Rh]
N
F
SO
2 Ph
SO
2 Ph
H H
TS15
TS16
9
TS18
F
Ligand
exchange
[Rh] =
O
Rh
O
O
O
O
Rh
O
O
O
O
Scheme 7
Catalytic cycle of Rh-catalyzed oxyamino-fluorination proposed on the basis of DFT calculations [93]
50
B. K. Mai and F. Himo