Pd-Catalyzed Suzuki-Miyaura Cross-Coupling of Arylboronic Acids and α-Iminonitriles through C-CN Bond Activation

2018 ◽  
Vol 2018 (34) ◽  
pp. 4769-4775 ◽  
Author(s):  
Kui Liu ◽  
Shou-Wei Tao ◽  
Chun Qian ◽  
Yong-Ming Zhu
Keyword(s):  
Bond Activation ◽  
Cross Coupling ◽  
Arylboronic Acids

scholarly journals Cross coupling of benzylammonium salts with boronic acids using a well-defined N-heterocyclic carbene–palladium(ii) precatalyst

RSC Advances ◽  
2019 ◽  
Vol 9 (10) ◽  
pp. 5738-5741 ◽  
Author(s):  
Tao Wang ◽  
Jiarui Guo ◽  
Xiaojuan Wang ◽  
Han Guo ◽  
Dingli Jia ◽  
...  
Keyword(s):  
Bond Activation ◽  
Cross Coupling ◽  
Boronic Acids ◽  
Arylboronic Acids

N-heterocyclic carbene–palladium(ii)-catalyzed cross-coupling of benzylammonium salts with arylboronic acids for the synthesis of diarylmethane derivatives via C–N bond activation has been developed.

scholarly journals 2,2-difluorovinyl benzoates for diverse synthesis of gem-difluoroenol ethers by Ni-catalyzed cross-coupling reactions

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Bingnan Du ◽  
Chun-Ming Chan ◽  
Pui-Yiu Lee ◽  
Leong-Hung Cheung ◽  
Xin Xu ◽  
...  
Keyword(s):  
Functional Group ◽  
Bond Activation ◽  
Cross Coupling ◽  
Building Blocks ◽  
Bioactive Molecules ◽  
Metallic Zinc ◽  
Coupling Reactions ◽  
Arylboronic Acids ◽  
Drug Candidates ◽  
Cross Coupling Reactions

Abstractgem-Difluoroalkene is a bioisostere of carbonyl group for improving bioavailability of drug candidates. Herein we develop structurally diverse 2,2-difluorovinyl benzoates (BzO-DFs) as versatile building blocks for modular synthesis of gem-difluoroenol ethers (44 examples) and gem-difluoroalkenes (2 examples) by Ni-catalyzed cross coupling reactions. Diverse BzO-DFs derivatives bearing sensitive functional groups (e.g., C = C, TMS, strained carbocycles) are readily prepared from their bromodifluoroacetates and bromodifluoroketones precursors using metallic zinc as reductant. With Ni(COD)2 and dppf [1,1’-bis(diphenylphosphino)ferrocene] as catalyst, reactions of BzO-DFs with arylboronic acids and arylmagnesium/alkylzinc reagents afforded the desired gem-difluoroenol ethers and gem-difluoroalkenes in good yields. The Ni-catalyzed coupling reactions features highly regioselective C(vinyl)–O(benzoate) bond activation of the BzO-DFs. Results from control experiments and DFT calculations are consistent with a mechanism involving initial oxidative addition of the BzO-DFs by the Ni(0) complex. By virtue of diversity of the BzO-DFs and excellent functional group tolerance, this method is amenable to late-stage functionalization of multifunctionalized bioactive molecules.

scholarly journals Heterogeneous Suzuki–Miyaura coupling of heteroaryl ester via chemoselective C(acyl)–O bond activation

RSC Advances ◽  
2019 ◽  
Vol 9 (30) ◽  
pp. 17266-17272 ◽  
Author(s):  
Hongpeng Ma ◽  
Chaolumen Bai ◽  
Yong-Sheng Bao
Keyword(s):  
Bond Activation ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Palladium Nanoparticle ◽  
Arylboronic Acids ◽  
Cross Coupling Reaction ◽  
Supported Palladium ◽  
A Site ◽  
Site Selective

A site-selective supported palladium nanoparticle catalyzed Suzuki–Miyaura cross-coupling reaction with heteroaryl esters and arylboronic acids as coupling partners was developed.

scholarly journals Cu(OTf)2‐Mediated Cross‐Coupling of Nitriles and N‐Heterocycles with Arylboronic Acids to Generate Nitrilium and Pyridinium Products

2021 ◽  
Author(s):  
Allan J. B. Watson ◽  
Nicola L. Bell ◽  
Chao Xu ◽  
James W. B. Fyfe ◽  
Julien C. Vantourout ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Arylboronic Acids

scholarly journals Cross‐Coupling of Aryl/Alkenyl Pivalates with Organozinc Reagents through Nickel‐Catalyzed CO Bond Activation under Mild Reaction Conditions

2009 ◽  
Vol 48 (8) ◽  
pp. 1351-1351
Author(s):  
Bi‐Jie Li ◽  
Yi‐Zhou Li ◽  
Xing‐Yu Lu ◽  
Jia Liu ◽  
Bing‐Tao Guan ◽  
...  
Keyword(s):  
Bond Activation ◽  
Cross Coupling ◽  
Reaction Conditions ◽  
Organozinc Reagents

Novel and Unexpected Deamination during the Palladium-Catalysed Cross-Coupling of Haloanilines and Arylboronic Acids

Synlett ◽  
1999 ◽  
Vol 1999 (4) ◽  
pp. 438-440 ◽  
Author(s):  
Michael Hird ◽  
Alexander J. Seed ◽  
Kenneth J. Toyne
Keyword(s):  
Cross Coupling ◽  
Arylboronic Acids
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