Table 3.

Optimization table for the Suzuki-coupling reaction on porphyrin 11.

Entry	Catalyst/ligand	Cat. mol % per C–Br	Base (24 equiv)	Temp. (ºC)	Time	Boronic acid/ester (3 equiv per C–Br)	Product detected by HRMS
1	Pd2dba3/SPhos	6.25%	K3PO4	110 °C	48 h	14	no
2	Pd2dba3/SPhos	6.25%	K3PO4	130 ºC	48 h	14	no
3	Pd2dba3/SPhos	12.5%	Cs2CO3	110 °C	48 h	14	no
4	Pd2dba3/Xantphos	12.5%	Cs2CO3	110 °C	48 h	14	no
5	Pd2dba3/Rac BINAP	12.5%	Cs2CO3	110 °C	48 h	14	no
6	Pd2dba3/SPhos	100%	Cs2CO3	85 °C	7 days	14 a	no
7	Pd(dppf)Cl2	2%	Cs2CO3	100 °C	20 h	20 b	no
8	Pd(PPh3)4	5%	Cs2CO3	100 °C	20 h	20 b	no
9	Pd(PPh3)4	12.5%	Na2CO3	120 °C	2 h	21 c	no
10	Pd(PPh3)4	12.5%	Cs2CO3	100 °C	48 h	21	no
11	Pd2dba3/SPhos	12.5%	Cs2CO3	85 °C	48 h	22	no
12	Pd2dba3/SPhos	6.25%	Cs2CO3	85 °C	24 h	25	no

^a12 equiv of boronic acid used in this reaction per C–Br. ^bAlternative procedure for Suzuki–Miyaura coupling [34]. ^cMicrowave irradiation instead of conventional heating was used [48].