Ni-Catalyzed C-H Cyanation of (Hetero)arenes with 2-Cyanoisothiazolidine 1,1-Dioxide as a Cyanation Reagent
A nickel-catalyzed C-H cyanation reaction of arenes has been developed using 2-cyanoisothiazolidine 1,1-dioxide as an electrophilic cyanation reagent. Many different directing groups can be used in this cyanation to obtain a series of cyanation products with good yields. Adopting this strategy to introduce a cyano group, natural alkaloid menisporphine was successfully synthesized through cyano group conversion that further proved the practicality of this cyanation method.
Rhodium catalyzed cyanation of chelation assisted C-H bonds
A rhodium-catalyzed cyanation of chelation assisted C-H bonds is described employing N-cyano-N-phenyl-p-methylbenzenesulfonamide as an efficient cyanating reagent. The present method allowed the synthesis of various benzonitirle derivatives in good to excellent yield. A number of chelating groups are also effective in the present cyanation of C-H bonds. In addition, the developed methodology was applied in the formal synthesis of the isoquinoline alkaloid, menisporphine.
Palladium-catalyzed Suzuki-Miyaura coupling of pyridyl-2-boronic esters with aryl halides using highly active and air-stable phosphine chloride and oxide ligands
(Chemical Equation Presented) The palladium-catalyzed Suzuki-Miyaura coupling of pyridyl-2-boronic esters provided an efficient approach to useful biaryl building blocks containing a 2-pyridyl moiety. The convenient reaction protocol demonstrates its pote
Yang, David X.,Colletti, Steven L.,Wu, Kevin,Song, Maoying,Li, George Y.,Shen, Hong C.
supporting information; experimental part
p. 381 - 384
(2009/07/11)
A general and efficient method for the Suzuki-Miyaura coupling of 2-pyridyl nucleophiles
(Chemical Equation Presented) One of the most general systems for the cross-coupling of aryl and heteroaryl bromides and chlorides with 2-pyridyl-derived nucleophiles has been developed, for which catalysts comprising [Pd2(dba)3] and either diaryl (1) or dialkyl phosphine oxide (2) supporting ligands were found to be ideal (see scheme).
Billingsley, Kelvin L.,Buchwald, Stephen L.
supporting information; body text
p. 4695 - 4698
(2009/02/06)
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