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. 2021 Jun 21;143(25):9682–9693. doi: 10.1021/jacs.1c05294

Table 2. Changes in Conversion of 1 and Product Site-Selectivity Outcomes, upon Changing Reaction Variables in Kumada Cross-Couplings (Scheme 5).

Entry Pd(OAc)2:nPPh3 Catalyst prestir time (h) n-Oct4NBr Conv (%)a 3cC2Ar:3cC4Ar:3cdiaryla
1 No cat. 0.5 – 0 N/A
2 1:4 0.5 – 100 83:0:17
3 1:2 0.5 – 100 91:3:6
4 1:1 0.5 – 99 84:6:9
5 1:1 24 – 85 80:11:8
6 1:1 0.5 + 83 21:68:12
7 1:1 24 + 96 15:77:8
8 1:4 0.5 + 96 67:26:7
a

Determined by 1H NMR of the crude reaction mixture after 1 h.