Dual Role of Acetanilides: Traceless Removal of a Directing Group through Deacetylation/Diazotation and Palladium-Catalyzed C–C-Coupling Reactions

2015 ◽  
Vol 80 (9) ◽  
pp. 4223-4234 ◽  
Author(s):  
Bernd Schmidt ◽  
Nelli Elizarov ◽  
Uwe Schilde ◽  
Alexandra Kelling
Keyword(s):  
Dual Role ◽  
Coupling Reactions ◽  
Palladium Catalyzed ◽  
Directing Group

scholarly journals Palladium-catalyzed Suzuki-Miyaura coupling of thioureas or thioamides

2019 ◽  
Vol 10 (1) ◽  
Author(s):  
Shaoyu Mai ◽  
Wendong Li ◽  
Xue Li ◽  
Yingwei Zhao ◽  
Qiuling Song
Keyword(s):  
Silver Salt ◽  
Coupling Reaction ◽  
Coupling Reactions ◽  
Mechanistic Studies ◽  
Aromatic Rings ◽  
Cross Coupling Reactions ◽  
Broad Array ◽  
Palladium Catalyzed

AbstractCross-coupling reactions involving metal carbene intermediates play an increasingly important role in C–C bond formation. Expanding the carbene precursors to a broader range of starting materials and more diverse products is an ongoing challenge in synthetic organic chemistry. Herein, we report a Suzuki-Miyaura coupling reaction of in situ-generated Pd–carbene complexes via desulfurization of thioureas or thioamides. This strategy enables the preparation of a broad array of substituted amidinium salts and unsymmetrical diaryl ketones. The reaction is readily scalable, compatible with bromo groups on aromatic rings, tolerant to moisture and air and has a broad substrate scope. Furthermore, a single crystal structure of Pd-diaminocarbene complex is obtained and proven to be the key intermediate in both catalytic and stoichiometric reactions. Preliminary mechanistic studies demonstrate the dual role of the silver salt as a desulfurating reagent assisting the elimination of sulfur and as oxidant facilitating the PdII/Pd0/PdII catalytic cycle.

Dual Role of H2O2 in Palladium-Catalyzed Dioxygenation of Terminal Alkenes

2017 ◽  
Vol 19 (13) ◽  
pp. 3354-3357 ◽  
Author(s):  
Jiuzhong Huang ◽  
Jianxiao Li ◽  
Jia Zheng ◽  
Wanqing Wu ◽  
Weigao Hu ◽  
...  
Keyword(s):  
Dual Role ◽  
Terminal Alkenes ◽  
Palladium Catalyzed

Dual Role of Anthranils as Amination and Transient Directing Group Sources: Synthesis of 2-Acyl Acridines

2018 ◽  
Vol 20 (13) ◽  
pp. 4010-4014 ◽  
Author(s):  
Saegun Kim ◽  
Sang Hoon Han ◽  
Neeraj Kumar Mishra ◽  
Rina Chun ◽  
Young Hoon Jung ◽  
...  
Keyword(s):  
Dual Role ◽  
Directing Group

ChemInform Abstract: Highly Efficient Carbopalladation Across Vinylsilane: Dual Role of the 2-PyMe2Si Group as a Directing Group and as a Phase Tag.

ChemInform ◽  
2001 ◽  
Vol 32 (16) ◽  
pp. no-no
Author(s):  
Kenichiro Itami ◽  
Koichi Mitsudo ◽  
Toshiyuki Kamei ◽  
Tooru Koike ◽  
Toshiki Nokami ◽  
...  
Keyword(s):  
Dual Role ◽  
Highly Efficient ◽  
Directing Group

scholarly journals A dual role for acetohydrazide in Pd-catalyzed controlled C(sp3)–H acetoxylation of aldehydes

RSC Advances ◽  
2020 ◽  
Vol 10 (21) ◽  
pp. 12192-12196
Author(s):  
Juan Chen ◽  
Chaolumen Bai ◽  
XingWen Tong ◽  
Dan Liu ◽  
Yong-Sheng Bao
Keyword(s):  
Dual Role ◽  
Group Approach ◽  
Palladium Catalyzed ◽  
Directing Group ◽  
First Time

The palladium catalyzed aldehyde directed acetoxylation of C(sp3)–H bonds was realized by a transient directing group approach for the first time.

Sign in / Sign up

Export Citation Format

Share Document