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. Author manuscript; available in PMC: 2009 Dec 5.
Published in final edited form as: J Org Chem. 2008 Dec 5;73(23):9508–9510. doi: 10.1021/jo8020049

Table 2.

Conversion of alkenes to pinacolboronates 11 using 1

graphic file with name nihms-86560-t0005.jpg
Entry R, R’ R” Equiv 1
(PyBH2I)		 Yield(a),(b)
1 nC8H17, H H 2 40%
2 nC10H21, H H 2 40%
3 Ph, H H 2 50%
4 BzO(CH2)4, H H 2 26%
5 BzO(CH2)4, H H 6 55%
6 norbornene H 2 47%
7 norbornene H 6 68%
8 -C4H8- H 1.5 67%
9 -C4H8- Ph 2 67%(c)
(a)

HB in DCM at RT, 2 h, followed by stirring with pinacol and NaOH (2-fold and 3-fold excess, respectively, relative to 1), 15 h, unless noted; isolated yields.

(b)

The pinacol boronates from entries 1-3 and 6-9 have been described previously and were identified by NMR comparisons; see Supporting Information for references.

(c)

HB required 15 h to go to completion.