Table 1 Selected attempts in condition optimizationsa.

From: Manipulations of phenylnorbornyl palladium species for multicomponent construction of a bridged polycyclic privileged scaffold

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No.

[Pd]

Ligand

Base

Solvent

Yield 2b (%)

Yield 1b (%)

1

Pd(OAc)2

PPh3

Cs2CO3

MeCN

48

3

2

Pd(OAc)2

PPh3

Cs2CO3

Toluene

59

6

3

Pd(OAc)2

PPh3

KOAC

Toluene

37

36

4

Pd(OAc)2

PPh3

K3PO4

Toluene

45

16

5

Pd(OAc)2

TFP

Cs2CO3

Toluene

93

Trace

6

Pd(OAc)2

RuPhos

Cs2CO3

Toluene

9

28

7

Pd2(dba)3

TFP

Cs2CO3

Toluene

35

31

8

Pd(PPh3)4

—

Cs2CO3

Toluene

32

38

9

Pd(dppf)Cl2

—

Cs2CO3

Toluene

37

24

10

Pd(OAc)2

TFP

Cs2CO3

THF

19

23

11

Pd(OAc)2

TFP

Cs2CO3

DMF

69

Trace

12

Pd(OAc)2

TFP

Cs2CO3

DME

75

Trace

  1. aUnless indicated otherwise, 2-iodo-N-methylaniline (1.0 eq.), NBE-5,6-diCOOiPr (1.0 eq.), morpholino benzoate (1.3 eq.), Pd (pre)catalyst (5% eq.), ligand (10% eq.), base (2.5 eq.), 100 oC, 12 h.
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