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 ◽  
...  

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.

RSC Advances ◽  
2018 ◽  
Vol 8 (70) ◽  
pp. 40000-40015 ◽  
Author(s):  
Nedra Touj ◽  
Abdullah S. Al-Ayed ◽  
Mathieu Sauthier ◽  
Lamjed Mansour ◽  
Abdel Halim Harrath ◽  
...  

The in situ prepared four component system Pd(OAc)2, 1,3-dialkylbenzimidazolium halides 2a–i and 4a–i, K2CO3 under CO atmosphere catalyses carbonylative cross-coupling reaction of 2-bromopyridine with various boronic acids to yield unsymmetrical arylpyridine ketones.


2020 ◽  
Vol 18 (13) ◽  
pp. 2447-2458 ◽  
Author(s):  
Amit Bhowmik ◽  
Mahesh Yadav ◽  
Rodney A. Fernandes

A mild and easy to operate NiCl2/2,2′-bipyridine-catalyzed cross-coupling of thiophenols with arylboronic acids has been developed for the synthesis of symmetric and unsymmetric diarylsulfides at room temperature and in air.


2016 ◽  
Vol 52 (65) ◽  
pp. 10040-10043 ◽  
Author(s):  
Thomas Cornilleau ◽  
Philippe Hermange ◽  
Eric Fouquet

Combining gold catalysis and photoredox processes allowed the synthesis of biaryl compounds from diazonium salts and boronic acids under mild conditions.


2016 ◽  
Vol 14 (24) ◽  
pp. 5690-5707 ◽  
Author(s):  
Guangrong Meng ◽  
Michal Szostak

A unified strategy for the palladium-catalyzed Suzuki–Miyaura cross-coupling of amides with boronic acids for the synthesis of ketones by N–C bond activation is reported.


2018 ◽  
Vol 2018 (34) ◽  
pp. 4769-4775 ◽  
Author(s):  
Kui Liu ◽  
Shou-Wei Tao ◽  
Chun Qian ◽  
Yong-Ming Zhu

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Bingnan Du ◽  
Chun-Ming Chan ◽  
Pui-Yiu Lee ◽  
Leong-Hung Cheung ◽  
Xin Xu ◽  
...  

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.


Synthesis ◽  
2018 ◽  
Vol 50 (16) ◽  
pp. 3187-3196 ◽  
Author(s):  
Marco Bandini ◽  
Yang Liu ◽  
Mario Daka

The Ni(II)-catalyzed cross-coupling of arylboronic acids with allenoates is documented. The high regio- and stereoselectivity of the process enables a wide range of β-aryl β,γ-unsaturated esters to be prepared in good to excellent yields (up to 95%) and high E/Z-selectivity. Additionally, [3+2]-cascade sequence was observed when 2-formylphenylboronic acid was employed.


RSC Advances ◽  
2019 ◽  
Vol 9 (30) ◽  
pp. 17266-17272 ◽  
Author(s):  
Hongpeng Ma ◽  
Chaolumen Bai ◽  
Yong-Sheng Bao

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


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