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. 2020 May 25;11(23):6031–6035. doi: 10.1039/d0sc01641a

Optimization of reaction conditionsa.

graphic file with name d0sc01641a-u1.jpg
Entry “Me” reagent Catalyst Ligand Base Yieldb (%)
1 TMB Pd(acac)2 SIPr Cs2CO3 n.d.
2 TMB Pd(acac)2 dppb Cs2CO3 n.d.
3 TMB Pd(acac)2 DavePhos Cs2CO3 n.d.
4 TMB Pd(acac)2 XPhos Cs2CO3 18
5 TMB Pd(acac)2 BrettPhos Cs2CO3 80
6c TMB Pd(acac)2 BrettPhos Cs2CO3 43
7d TMB Pd(acac)2 BrettPhos Cs2CO3 53
8 TMB Pd(acac)2 BrettPhos K3PO4 25
9 TMB Pd(acac)2 BrettPhos CsF 32
10 TMB Pd(OAc)2 BrettPhos Cs2CO3 54
11 TMB Pd2(dba)3 BrettPhos Cs2CO3 50
12 ZnMe2 Pd(acac)2 BrettPhos Cs2CO3 n.d.
13 MeMgBr Pd(acac)2 BrettPhos Cs2CO3 n.d.
14 DIBAL-Me3 Pd(acac)2 BrettPhos Cs2CO3 n.d.
15e MeB(OH)2 Pd(acac)2 BrettPhos Cs2CO3 55
16 TMB — BrettPhos Cs2CO3 n.d.
a

Reaction conditions: 1a (0.2 mmol, 1 equiv.), “Me” reagent (1.75 equiv.), catalyst (5 mol%), ligand (15 mol%) and base (2 equiv.) in toluene (0.6 mL) at 150 °C for 24 h under N2.

b

Isolated yields.

c

1,4-Dioxane as the solvent.

d

130 °C.

e

5 equiv. of MeB(OH)2. DABAL-Me3 = bis(trimethylaluminum)-1,4-diazabicyclo[2.2.2]octane adduct.