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. Author manuscript; available in PMC: 2020 Jul 22.
Published in final edited form as: Angew Chem Int Ed Engl. 2019 Jun 24;58(30):10245–10249. doi: 10.1002/anie.201905021

Table 1.

Optimization of reaction conditions.[a]

graphic file with name nihms-1030418-t0005.jpg
entry x (eq.) [Pd] ligand yield (%)[b]
1 2.5 Pd(PPh3)4 – 35
2 2.5 Pd(dba)2 dppf <5
3 2.5 Pd(dba)2 P(p-FC6H4)3 34
4 2.5 Pd(dba)2 P(p-MeC6H4)3 <5
5 2.5 Pd(dba)2 P(o-MeC6H4)3 63
6 1.5 Pd(dba)2 P(o-MeC6H4)3 63
7[c] 1.5 Pd(dba)2 P(o-MeC6H4)3 61
8[c,d] 1.5 Pd(dba)2 P(o-MeC6H4)3 78 (75)
[a]

Reaction conditions: benzene (5, 5.0 mmol, 10 eq.), MTAD (1, 0.5 mmol, 1.0 eq.), CH2Cl2 (0.1 M), visible light, –78 ºC; then addition of PhMgBr (3.0 M in Et2O), [Pd] catalyst in THF.

[b]

Determined by 1H NMR analysis relative to the internal standard. Isolated yield shown in parentheses.

[c]

CH2Cl2 (0.2 M).

[d]

Substitution step was conducted from –50 to 15 ºC over 10 h.