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. Author manuscript; available in PMC: 2014 Jul 5.
Published in final edited form as: J Org Chem. 2013 Jun 18;78(13):6471–6487. doi: 10.1021/jo400469t

Table 3.

Suzuki-Miyaura Coupling (SMC) Reaction

graphic file with name nihms-495857-t0003.jpg

ArX Pd Sourcea,b Ligandc,d Basee,f Solventg Temp. (°C)/Time (h) Results
1 36a Pd(OAc)2 DCPB K3PO4 dioxane:H2O 100/24 35 + 36a
2 37a Pd(OAc)2 DCPB K3PO4 dioxane:H2O 100/24 35 + 37a
3 36a Pd(OAc)2 DCPB CsF dioxane 100/24 35 + 36a
4 36a Pd(OAc)2 XPhos K3PO4 Tol:H2O 100/24 35 + 36a
5 36a Pd(OAc)2 DavePhos K3PO4 Tol:H2O 100/24 35 + 36a
6 36a Pd(OAc)2 SPhos K3PO4 Tol:H2O 100/24 35 + 36a
7 36a Pd(OAc)2 SPhos K3PO4 THF:H2O 50/24 38a (20%)+38b (10%) + 35 (15%) + 36a (13%)
8 36a Pd(OAc)2 SPhos K3PO4 THF:H2O 50/48 38a (37%) + 38b (18%) + 35 (20%)
9 36a Pd2(dba)3 SPhos K3PO4 THF:H2O 50/48 38a (38%) + 38b (19%) + 35 (20%)
a

5 mo % of Pd(OAc)2;

b

2.5 mol % of Pd2(dba)3;

c

Ligands: DCPB: 2-(Dicyclohexylphosphanyl)biphenyl; XPhos: 2-Dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl; DavePhos: 2-Dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl; SPhos: 2-Dicyclohexylphosphino-2′6′-dimethoxybiphenyl;

d

20 mol % of ligand;

e

2 equiv. of K3PO4;

f

8 equiv. of CsF;

g

solvent:H2O/10:1.