1517-60-8Relevant articles and documents
Nickel-Catalyzed Addition of Aryl Bromides to Aldehydes to Form Hindered Secondary Alcohols
Garcia, Kevin J.,Gilbert, Michael M.,Weix, Daniel J.
supporting information, p. 1823 - 1827 (2019/02/14)
Transition-metal-catalyzed addition of aryl halides across carbonyls remains poorly developed, especially for aliphatic aldehydes and hindered substrate combinations. We report here that simple nickel complexes of bipyridine and PyBox can catalyze the addition of aryl halides to both aromatic and aliphatic aldehydes using zinc metal as the reducing agent. This convenient approach tolerates acidic functional groups that are not compatible with Grignard reactions, yet sterically hindered substrates still couple in high yield (33 examples, 70% average yield). Mechanistic studies show that an arylnickel, and not an arylzinc, adds efficiently to cyclohexanecarboxaldehyde, but only in the presence of a Lewis acid co-catalyst (ZnBr2).
AlCl3 catalyzed coupling of: N-benzylic sulfonamides with 2-substituted cyanoacetates through carbon-nitrogen bond cleavage
Hu, Chen,Hong, Gang,Qian, Xiaofei,Kim, Kwang Rim,Zhu, Xiaoyan,Wang, Limin
supporting information, p. 4984 - 4991 (2017/07/10)
A new cross-coupling reaction of N-benzylic sulfonamides with 2-substituted cyanoacetates for the synthesis of 2-substituted benzylbenzene was reported. In the presence of AlCl3, a broad range of N-benzylic sulfonamides reacted smoothly with 2-substituted cyanoacetates to afford structurally diverse benzylbenzenes in moderate to excellent yields. The conversion could be enlarged to gram-scale efficiently. The practicability of this approach was further manifested in the synthesis of a related bioactive agent with high anti-inflammatory activity.
Mesityllithium and p-(dimethylamino)phenyllithium for the selective alternate trilithiation of the hexaphenylbenzene framework
Kojima, Tatsuo,Hiraoka, Shuichi
supporting information, p. 10420 - 10423 (2014/10/15)
We report mesityllithium and p-(dimethylamino)phenyllithium as new valuable lithiating reagents, which realize Br/Li exchange reaction of bromoarenes at relatively high temperature in THF. With these reagents, we established the general and practical protocols for the selective alternate trilithiation of the hexaphenylbenzene framework. This journal is the Partner Organisations 2014.