1 h 4 16 4 25 m 1 h 5 89 s 2 h 7 41 7 49 m 5 h 7 58 tt 2 h 8 06 8 09 m 2 h 8 09 8 12 m 2 h 8 24 t 1 h 8 59 d 1 h 8 69 d 1 h 8 69 d 1 h 13 c nmr 400 mhz methanol d 4 u03b4 13 91 20 96 31 01 37 64 55 73 73 22 128 10 129 51 129 56 133 04 138 93 147 93 151 19 165 56 169 74 bis pinacolato diboron 4 70 kg 18 49 mol 0 75 equiv 4 4 u2032 di tert butyl 2 2 u2032 dipyridyl 0 41 kg 1 48 mol 0 06 equiv and s nicotine i 4 00 kg 24 66 mol 1 00 equiv were added to anhydrous tetrahydrofuran 40 00 l in a nitrogen purged reactor nitrogen was bubbled vigorously into the colorless solution for 30 minutes before and after charging chloro 1 5 cyclooctadiene iridium i dimer 0 50 kg 0 74 mol 0 03 equiv a nitrogen sweep of the headspace was maintained as the mixture was heated and held at 60 u00b0 c for 18 hours gc ms analysis indicated gt 95 conversion to the borinate ester ii from nicotine i the solution was concentrated under vacuum tetrahydrofuran was replaced.