TY - JOUR
T1 - Iridium-Catalyzed C-H Amination of Weinreb Amides
T2 - A Facile Pathway toward Anilines and Quinazolin-2,4-diones
AU - Dong, Xunqing
AU - Ma, Panpan
AU - Zhang, Tao
AU - Jalani, Hitesh B.
AU - Li, Guigen
AU - Lu, Hongjian
N1 - Publisher Copyright:
© 2020 American Chemical Society. All rights reserved.
Copyright:
Copyright 2020 Elsevier B.V., All rights reserved.
PY - 2020/10/16
Y1 - 2020/10/16
N2 - C-H amination of arenes directed by weakly coordinating Weinreb amides has been achieved with an iridium catalyst and 2,2,2-trichloroethoxycarbonyl (Troc) azide as an aminating agent, providing a robust method of producing synthetic useful ortho-TrocNH aryl Weinreb amides. Taking advantage of the reactivity of Weinreb amide and Troc groups in the amination products, selective hydrolysis was achieved as an attractive process for the synthesis of ortho-NH2 aryl Weinreb amides, which are the building blocks useful in the synthesis of bioactive compounds, and cascade aminocyclization with primary amines was successful and provided an efficient pathway for the construction of quinazolin-2,4-diones, which are present in various alkaloids and natural products.
AB - C-H amination of arenes directed by weakly coordinating Weinreb amides has been achieved with an iridium catalyst and 2,2,2-trichloroethoxycarbonyl (Troc) azide as an aminating agent, providing a robust method of producing synthetic useful ortho-TrocNH aryl Weinreb amides. Taking advantage of the reactivity of Weinreb amide and Troc groups in the amination products, selective hydrolysis was achieved as an attractive process for the synthesis of ortho-NH2 aryl Weinreb amides, which are the building blocks useful in the synthesis of bioactive compounds, and cascade aminocyclization with primary amines was successful and provided an efficient pathway for the construction of quinazolin-2,4-diones, which are present in various alkaloids and natural products.
UR - http://www.scopus.com/inward/record.url?scp=85096495157&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.0c01789
DO - 10.1021/acs.joc.0c01789
M3 - Article
AN - SCOPUS:85096495157
VL - 85
SP - 13096
EP - 13107
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 20
ER -