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The Palladium‐Catalyzed Cross‐Coupling Reactions of Organotin Reagents with Organic Electrophiles [New Synthetic Methods (58)]
Author(s) -
Stille John K.
Publication year - 1986
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198605081
Subject(s) - electrophile , palladium , carbon monoxide , regioselectivity , organic synthesis , chemistry , coupling reaction , reagent , ketone , stereospecificity , combinatorial chemistry , catalysis , organic chemistry
The cross‐coupling of organotin reagents with a variety of organic electrophiles, catalyzed by palladium, provides a novel method for generating a carbon‐carbon bond. Because this mild, versatile reaction is tolerant of a wide variety of functional groups on either coupling partner, is stereospecific and regioselective, and gives high yields of product, it is ideal for use in the synthesis of elaborate organic molecules. When the coupling reaction is carried out in the presence of carbon monoxide, instead of a direct coupling, carbon monoxide insertion takes place, stitching the two coupling partners together and generating a ketone.