61822-18-2Relevant articles and documents
Fine-tuning hydroxylamines as single-nitrogen sources for Pd(0)-catalyzed diamination of o-bromo(or chloro)-biaryls
Bai, Jiaxing,Ding, Pin,Han, Lingbo,Liu, Jingjing,Luan, Xinjun
, (2022/03/19)
Transition metal-catalyzed diamination by hydroxylamines is a common approach for making three-membered aziridines, while its use for building the larger N-heterocycles is still underdeveloped. Herein, we report an efficient Pd(0)-catalyzed inter-molecular [4+1] annulation of o-bromo(or chloro)-biaryls with bifunctional secondary hydroxylamines for the one-step assembly of synthetically useful carbazoles. Noteworthily, a linchpin for this domino reaction was the judicious selection of both the amino-sources and Pd(0)-catalysts for enabling the prerequisite oxidative addition of aryl halides to Pd(0)-species in the presence of hydroxylamines with a labile N-O bond. [Figure not available: see fulltext.].
"on Water" Promoted Ullmann-Type C-N Bond-Forming Reactions: Application to Carbazole Alkaloids by Selective N-Arylation of Aminophenols
Chakraborti, Gargi,Paladhi, Sushovan,Mandal, Tirtha,Dash, Jyotirmayee
, p. 7347 - 7359 (2018/07/29)
The Ullmann-type cross coupling of a variety of aromatic, aliphatic amines with aryl halides is reported using a CuI-based catalytic system in combination with an easily accessible prolinamide ligand in aqueous media. The method is mild and tolerant to air, moisture, and a wide range of functional groups, providing a novel way to access a variety of aminated products. Secondary amines like heteroaromatic amines and nucleobases have also been used, affording the corresponding coupling products in good to excellent yields. Moreover, this method has been employed for chemoselective C-N arylation of aminophenols and further utilized for the synthesis of carbazole natural products, avoiding the protection and deprotection steps.
Visible-Light-Induced Synthesis of Carbazoles by in Situ Formation of Photosensitizing Intermediate
Chatterjee, Tanmay,Roh, Geum-Bee,Shoaib, Mahbubul Alam,Suhl, Chang-Heon,Kim, Jun Soo,Cho, Cheon-Gyu,Cho, Eun Jin
, p. 1906 - 1909 (2017/04/11)
A visible-light-induced synthesis of N-H carbazoles from easily accessible 2,2′-diaminobiaryls in the absence of any external photosensitizer is reported. The process only requires tBuONO and natural resources, visible light, and molecular oxygen for the synthesis of N-H carbazoles. Experimental and computational studies support that the in situ formation of a visible-light-absorbing photosensitizing intermediate, benzocinnoline N-imide, is responsible for the activation of triplet molecular oxygen to singlet oxygen that, in turn, promotes the synthesis of carbazole.
