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. 2021 Apr 14;12(20):7066–7072. doi: 10.1039/d1sc01349a

Optimization of the BCP Bpin cross-coupling reaction.

graphic file with name d1sc01349a-u2.jpg
Entry BCP Bpin Catalysta Solv., add. % 8b % 7 remainingb
1c 7a cataCXium A G2 PhMe (0.1 M) 5 71
2 7a cataCXium A G2 PhMe (0.1 M) 21 55
3 7i cataCXium A G2 CPME (0.1 M) 43 46
4 7i cataCXium A G2 CPME (0.4 M) 55 25
5 7i Pd(OAc)2/cataCXium A (1 : 2) CPME (0.4 M) 62 9
6 7b Pd(OAc) 2 /cataCXium A (1 : 2) CPME (0.4 M), Cu 2 O (1.0 equiv.) 69 (53% IY) 18
7 7b Pd(OAc)2/cataCXium A (1 : 2) CPME (0.4 M), Cu2O (2.0 equiv.) 56 8
a

CataCXium A: (n-Bu)P(1-Ad)2, di(1-adamantyl)-n-butylphosphine.

b

AY as determined by 1H NMR analysis of the crude reaction mixture against CH2Br2 as an internal standard.

c

Reaction performed at 100 °C, 0.1 M.