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. Author manuscript; available in PMC: 2020 Apr 3.
Published in final edited form as: Nature. 2019 Sep 25;573(7775):563–567. doi: 10.1038/s41586-019-1580-x

Table 1.

Evaluation of conditions for a Pd-catalyzed carbopalladation/carbonylation cascade.

entrya [Pd] mol % CO source additive N (min) 30 (%)b 31 (%)b 32 (%)b
1 Pd(P(o-Tol)3)2 50 CO (1 atm) 0 92 1 5
2 Pd(P(o-Tol)3)2 50 CO (1 atm) 20 67 11 15
3 Pd(P(o-Tol)3)2 120 CO (1 atm) 90 0 52 0
4 Pd(P(o-Tol)3)2 120 CO (10 atm) 90 0 53 0
5 Pd(PPh3)4 120 CO (1 atm) 90 23 48 13
6 Pd(PPh3)4 50 33 DBU 85 0 8
7 Pd(PPh3)4 50 34 90 0 0
8 Pd(PPh3)4 50 35 KF 14 7 4
9 Pd(PPh3)4 50 36 KF 22 31 10
10 Pd(PPh3)4 50 36 KF 1 57 14
11 Pd(P(o-Tol)3)2 50 36 KF 60 0 0
12 PdCl2(dppf) 50 36 KF 80 0 0
13 PdCl2(Xantphos) 50 36 KF 55 1 4
a

Reactions performed on 0.01 mmol scale at 100 °C.

b

Yields determined by 1H NMR versus pyrazine as an added internal standard.

DBU, 1,8-diazabicyclo[5.4.0]undec-7-ene; dppf, 1,1′-bis(diphenylphosphino)ferrocene; Xantphos, 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene