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. Author manuscript; available in PMC: 2009 Nov 1.
Published in final edited form as: J Comb Chem. 2008 Oct 21;10(6):941–947. doi: 10.1021/cc800120y

Scheme 3.

Scheme 3

Suzuki-Miyaura Coupling [8{1–13}], Carbonylative Suzuki Coupling [8{14}], Amination [8{15–20}], and Subsequent Iodocyclization [9{1–24}]

i. 5 mol % Pd(PPh3)4, K2CO3 (3.0 equiv), and ArB(OH)2 10{1,4,7–8} (1.5 equiv) in toluene/EtOH, 80 °C

ii. 5 mol % Pd(dba)2, 8 mol % PPh3, KOH (3.0 equiv), and (Het)ArB(OH)2 10{6} (1.5 equiv) in toluence/EtOH, 80 °C

iii. 5 mol % PdCl2(dppf), K2CO3 (3.0 equiv), NaI (3.0 equiv), CO (1.0 atm), and ArB(OH)2 10{1} (1.1 equiv) in toluene/EtOH, 80 °C

iv. 5 mol % Pd2(dba)3, DavePhos (0.1 equiv), NaOtBu (1.4 equiv), and amines 11 (1.5 equiv) in toluene, 60 °C