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. Author manuscript; available in PMC: 2017 May 4.
Published in final edited form as: J Am Chem Soc. 2016 Apr 22;138(17):5539–5542. doi: 10.1021/jacs.6b02914

Table 2.

Optimization of Alkenyl Boronic Ester Formation

graphic file with name nihms-784440-f0006.jpg
entry precatalyst (mol %) ligand (mol %) additive 2 (%)a 3 (%)a 4 (%)a
1 none none none 100 0 0
2 Pd2dba3 (5 mol %) Cy3P (20 mol %) none 53 15 32
3 Pd2dba3 (5 mol %) none none 0 35 65
4 Pd2dba3 (5 mol %) Ph3P (20 mol %) none 65 10 25
5 Pd2dba3 (5 mol %) SPhos (10 mol %) none 0 56 44
6 Pd2dba3 (5 mol %) tBuPPh2 (20 mol %) none 19 19 62
7 Pd2dba3 (5 mol %) L1 (20 mol %) none 2 16 82
8 Pd2dba3 (2.5 mol %) L1 (10 mol %) none 0 18 82
9b Pd2dba3 (2.5 mol %) L1 (10 mol %) LiOTfc 0 0 >99
10b (L1)2PdCl2 (2.5 mol %) none LiOTfc 0 0 >99
a

Yield determined by NMR.

b

90 °C.

c

1.5 equiv.