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BH 3 ⋅ Me 2 S: An Alternative Hydride Source for NiH‐Catalyzed Reductive Migratory Hydroarylation and Hydroalkenylation of Alkenes
Author(s) -
Liu Jiandong,
Gong Hegui,
Zhu Shaolin
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100005
Subject(s) - hydride , chemistry , regioselectivity , reductive elimination , catalysis , yield (engineering) , borane , selectivity , nickel , combinatorial chemistry , medicinal chemistry , organic chemistry , metal , physics , thermodynamics
Borane dimethylsulfide (BMS) was found to be an efficient hydride source for nickel‐hydride catalyzed reductive migratory hydrofunctionalization reactions. Catalytic reductive migratory hydroarylation and migratory hydroalkenylation were achieved with BMS in high yields and with excellent regioselectivity. A large‐scale experiment employing as little as 0.5 equivalents of BH 3 ⋅ Me 2 S as the hydride source delivered the desired migratory hydroarylation product in high yield and selectivity.