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. Author manuscript; available in PMC: 2012 May 6.
Published in final edited form as: J Org Chem. 2011 Apr 7;76(9):3571–3575. doi: 10.1021/jo200250y

TABLE 1.

Substrate scope of the two-step transesterification/hydrolysis of pinacolyl boronate esters.a

graphic file with name nihms287132u2.jpg
entry substrate 2 % yield of 2b 3 % yield of 3b
1 1a graphic file with name nihms287132t1.jpg graphic file with name nihms287132t2.jpg 85 graphic file with name nihms287132t3.jpg 95
2 1b graphic file with name nihms287132t4.jpg graphic file with name nihms287132t5.jpg 72 graphic file with name nihms287132t6.jpg 90
3 1c graphic file with name nihms287132t7.jpg graphic file with name nihms287132t8.jpg 88 graphic file with name nihms287132t9.jpg 92c
4 1d graphic file with name nihms287132t10.jpg graphic file with name nihms287132t11.jpg 75 graphic file with name nihms287132t12.jpg 96c
5 1e graphic file with name nihms287132t13.jpg graphic file with name nihms287132t14.jpg 84 graphic file with name nihms287132t15.jpg 90c
6 1f graphic file with name nihms287132t16.jpg graphic file with name nihms287132t17.jpg 65 graphic file with name nihms287132t18.jpg 98
7 1g graphic file with name nihms287132t19.jpg graphic file with name nihms287132t20.jpg 68 graphic file with name nihms287132t21.jpg 69c
8 1h graphic file with name nihms287132t22.jpg graphic file with name nihms287132t23.jpg 79 graphic file with name nihms287132t24.jpg 79c
9 1i graphic file with name nihms287132t25.jpg graphic file with name nihms287132t26.jpg 80 graphic file with name nihms287132t27.jpg 82
10 1j graphic file with name nihms287132t28.jpg graphic file with name nihms287132t29.jpg 76 graphic file with name nihms287132t30.jpg 31
11 1k graphic file with name nihms287132t31.jpg graphic file with name nihms287132t32.jpg 97 graphic file with name nihms287132t33.jpg 89c
a

Each reaction was performed at least twice. Conditions: 1 (1 equiv), DEA (1.1 equiv), ether, rt, ~30 minutes followed by 0.1M HCl (20 min).

b

Isolated yield.

c

Product was isolated as the pinacol ester.