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Furthermore, because mixtures of olefin isomers are
abundant industrial raw materials derived directly from
petrochemical sources and are substantially cheaper than pure
olefin isomers, their use in regioconvergent reactions to produce
value-added products is of considerable interest. As a proof-of-
concept, when using mixtures of octenes (equimolar amounts of
the five linear octene-isomers) on 10 mmol scale, it was possible
to lower the catalyst loading to 1 mol% without significantly
impacting the yield or the rr (Scheme 1).
Me
Me
Me
Me
1 mol% NiBr2
1.2 mol% L1
Me
Me
Me
+
Ph
I
n-Oct
Ph
2.5 equiv (EtO)3SiH
2.5 equiv KF
DMF (0.5 M), 25 oC, 24 h
2a
(1.5 equiv)
3a
81% yield, 22:1 rr
Me
Me
10 mmol (1:1:1:1:1)
petroleum-derived feedstocks
Scheme 1. Regioconvergent experiment with lower catalyst loading.
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Acknowledgements
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Support was provided by “1000-Youth Talents Plan”, NSFC
(21772087, 21602101). We thank Professors Yi-Ming Wang
(University of Pittsburgh) and Ruben Martin (ICIQ) for helpful
suggestions during the preparation of the manuscript.
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Keywords: nickel • C–H activation • isomerization • alkylation •
regioselectivity
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