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Iridium Complexes as Efficient Catalysts for Construction of α ‐Substituted Ketones via Hydrogen Borrowing of Alcohols in Water
Author(s) -
Luo Nianhua,
Zhong Yuhong,
Wen Huiling,
Shui Hongling,
Luo Renshi
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.202001550
Subject(s) - chemistry , iridium , catalysis , alkylation , yield (engineering) , solvent , hydrogen , organic chemistry , ketone , alcohol , base (topology) , combinatorial chemistry , mathematical analysis , materials science , mathematics , metallurgy
Ketones are of great importance in synthesis, biology, and pharmaceuticals. This paper reports an iridium complexes‐catalyzed cross‐coupling of alcohols via hydrogen borrowing, affording a series of α ‐alkylated ketones in high yield (86 %–95 %) and chemoselectivities (>99 : 1). This methodology has the advantages of low catalyst loading (0.1 mol%) and environmentally benign water as the solvent. Studies have shown the amount of base has a great impact on chemoselectivities. Meanwhile, deuteration experiments show water plays an important role in accelerating the reduction of the unsaturated ketones intermediates. Remarkably, a gram‐scale experiment demonstrates this methodology of iridium‐catalyzed cross‐coupling of alcohols has potential application in the practical synthesis of α ‐alkylated ketones.