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. Author manuscript; available in PMC: 2018 Oct 20.
Published in final edited form as: J Org Chem. 2017 Oct 2;82(20):11056–11071. doi: 10.1021/acs.joc.7b02004

Table 2.

Structure-Activity of Siloxane Polymer in Cross-Coupling Reactionsa

graphic file with name nihms913477u3.jpg
entry siloxane polymer time 1H-NMR resultsb
(6 : 5 : 7)
1 graphic file with name nihms913477t1.jpg 2 h 100 : nd : <1c
2 graphic file with name nihms913477t2.jpg 2 h 80 : nd : 20
3 graphic file with name nihms913477t3.jpg 50 h 1 : 99 : nd
4 graphic file with name nihms913477t4.jpg 20 h 42 : 33 : 25
5d graphic file with name nihms913477t5.jpg 20 h 6 : 94 : nd
6 graphic file with name nihms913477t6.jpg 2 h 83 : nd : 17
a

All reactions were performed on 0.3 mmol scale using 2.5 equiv PhLi, 3.0 equiv siloxane polymer, 3 mol % PdCl2, 4 mol % dpca, 10 mol % CuI.

b

Determined by 1H-NMR analysis of the reaction mixture following an aqueous workup, extraction with Et2O and polymer removal via precipitation in CH3CN.

c

98% yield of 6.

d

The insoluble polymer was stirred heterogeneously in reaction mixture. nd = not detected.