A Bulky Biaryl Phosphine Ligand Allows for Palladium-Catalyzed Amidation of Five-Membered Heterocycles as Electrophiles

The incredible bulk: The first palladium-catalyzed amidation of five-membered heterocyclic bromides with multiple heteroatoms was achieved using the Pd/1 catalyst system. N-Arylated imidazoles, pyrazoles, thiazoles, pyrroles, and thiophenes were synthesized in moderate to excellent yield. Experiment...

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Bibliographic Details
Main Authors: Su, Mingjuan (Contributor), Buchwald, Stephen Leffler (Contributor)
Other Authors: Massachusetts Institute of Technology. Department of Chemistry (Contributor)
Format: Article
Language:English
Published: Wiley Blackwell, 2013-11-01T16:18:48Z.
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Online Access:Get fulltext
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100 1 0 |a Su, Mingjuan  |e author 
100 1 0 |a Massachusetts Institute of Technology. Department of Chemistry  |e contributor 
100 1 0 |a Su, Mingjuan  |e contributor 
100 1 0 |a Buchwald, Stephen Leffler  |e contributor 
700 1 0 |a Buchwald, Stephen Leffler  |e author 
245 0 0 |a A Bulky Biaryl Phosphine Ligand Allows for Palladium-Catalyzed Amidation of Five-Membered Heterocycles as Electrophiles 
260 |b Wiley Blackwell,   |c 2013-11-01T16:18:48Z. 
856 |z Get fulltext  |u http://hdl.handle.net/1721.1/81944 
520 |a The incredible bulk: The first palladium-catalyzed amidation of five-membered heterocyclic bromides with multiple heteroatoms was achieved using the Pd/1 catalyst system. N-Arylated imidazoles, pyrazoles, thiazoles, pyrroles, and thiophenes were synthesized in moderate to excellent yield. Experimental results and DFT calculations point to the need for an electron-rich and sterically demanding biaryl phosphine ligand to promote these difficult reactions. 
520 |a National Institutes of Health (U.S.) (Grant GM58160) 
520 |a National Science Foundation (U.S.) (Grant CHE9808061) 
520 |a National Science Foundation (U.S.) (Grant DBI 9729592) 
520 |a National Science Foundation (U.S.) (CHE-0946721) 
546 |a en_US 
655 7 |a Article 
773 |t Angewandte Chemie International Edition