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Piperidine-appended imidazolium ionic liquid as task-specific basic-IL for Suzuki and Heck reactions and for tandem Wittig-Suzuki, Wittig-Heck, Horner-Emmons-Suzuki, and Horner-Emmons-Heck protocols
被引：33
|作者：
Savanur, Hemantkumar M.
[1
]
Kalkhambkar, Rajesh G.
[1
]
Laali, Kenneth K.
[2
]
机构：
[1] Karnatak Univ, Karnatak Sci Coll, Dept Chem, Dharwad 580001, Karnataka, India
[2] Univ North Florida, Dept Chem, 1 UNF Dr, Jacksonville, FL 32224 USA
关键词：
PAIM] [NTf2) as basic-IL;
BMIM] [X] as solvent;
Suzuki and Heck;
Wittig and Horner-Emmons;
Tandem protocols;
Bis-olefination;
COUPLING REACTIONS;
ARYLBORONIC ACIDS;
MIZOROKI-HECK;
EFFICIENT;
LIGAND;
ARYLATION;
CATALYST;
COMPLEXES;
D O I：
10.1016/j.apcata.2017.06.015
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ;
081704 ;
摘要：
Facile, high yielding, one-pot methods for the synthesis of a library of diversely substituted bi-aryls, diary-lethenes, and aryl-enoates, via Suzuki and Heck reactions, and by sequential Wittig-Suzuki, Wittig-Heck, Horner-Emmons-Suzuki, and Horner-Emmons-Heck reactions are reported. The reactions employ piperidine-appended imidazolium ionic liquid [PAIM][NTf2]as a task-specific basic-IL, butyl-methyl-imidazolium ionic liquid [BMIM] [X] (X = PF6, BF4) as solvent, and catalytic amounts of Pd(OAc)2, with no other additives. Wittig and Horner-Emmons reactions are effected by reacting substituted benzaldehydes with 4-bromobenzyl-PPh3 (or bromomethyl-PPh3) phosphonium salts, or diethylphosphonate with bromobenzaldehydes respectively, to form the corresponding ethenes. Subsequent cross-coupling reactions are accomplished by addition of aryl-boronic acid or phenyl-ethenes along with Pd(OAc)(2) to bring about the aforementioned hyphenated transformations. The feasibility to perform double-olefination via Wittig and Horner-Emmons reactions with dialdehydes to form highly conjugated bis-styryl and bis-enoate compounds is also shown. The [BMIM] [X] solvent is recycled and reused.
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页码：150 / 161
页数：12
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