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. Author manuscript; available in PMC: 2016 Feb 28.
Published in final edited form as: Chem Commun (Camb). 2015 Feb 28;51(17):3608–3611. doi: 10.1039/c4cc09107h

Table 1.

Synthesis of α-functionalized alkyl(MIDA)boronatesa

graphic file with name nihms661294u1.jpg
entry NuH product yield (%)
1b 6a graphic file with name nihms661294t1.jpg 7a graphic file with name nihms661294t2.jpg 99
2b 6b graphic file with name nihms661294t3.jpg 7b graphic file with name nihms661294t4.jpg 94
3 6c graphic file with name nihms661294t5.jpg 7c graphic file with name nihms661294t6.jpg 97
4c 6d graphic file with name nihms661294t7.jpg 7d graphic file with name nihms661294t8.jpg 91
5 6e graphic file with name nihms661294t9.jpg 7e graphic file with name nihms661294t10.jpg 99
6 6f graphic file with name nihms661294t11.jpg 7f graphic file with name nihms661294t12.jpg 78
7 6g graphic file with name nihms661294t13.jpg 7g graphic file with name nihms661294t14.jpg 98
8 6h graphic file with name nihms661294t15.jpg 7h graphic file with name nihms661294t16.jpg 96
9 6i graphic file with name nihms661294t17.jpg 7i graphic file with name nihms661294t18.jpg 85
10 6j graphic file with name nihms661294t19.jpg 7j graphic file with name nihms661294t20.jpg 92
a

Unless otherwise noted, reactions were conducted with alcohol (1.0 equiv.), 1.0 equiv. of acidic pronucleophile, 1.2 equiv. of triphenylphosphine, and 1.2 equiv. of DIAD in THF at 23 °C for 30 min.

b

1.5 equiv. of acidic pronucleophile, 1.5 equiv. of triphenylphosphine, and 1.5 equiv. of DIAD were used. Reaction time: 30 min. Temp.: 23 °C.

c

2.0 equiv. of acidic pronucleophile, 1.5 equiv. of triphenylphosphine, and 1.5 equiv. of DIAD were used. Reaction time: 12 h. Temp.: 23 °C.