32891-91-1Relevant academic research and scientific papers
Palladium-catalyzed cross-coupling of benzyltitanium(IV) reagents with aryl fluorides
Li, Yan
, (2022/01/11)
The first palladium-catalyzed cross-coupling between benzyltitanium(IV) reagents with aryl fluorides is reported. A variety of diarylmethanes can be prepared in good to excellent yields by the catalyst system of PdCl2(dppf)2 associated with 1-[2-(di-tert-butylphosphanyl)phenyl]-4-methoxypiperidine. This reaction offered a highly efficient approach to diarylmethanes that are commonly found in life-changing drug molecules. Graphical abstract: [Figure not available: see fulltext.]
Photoinduced NaI-Promoted Radical Borylation of Alkyl Halides and Pseudohalides
Wang, Chenglan,Zhou, Lu,Yang, Kai,Zhang, Feng,Song, Qiuling
, p. 1825 - 1830 (2021/05/28)
A method for photoinduced NaI-promoted radical borylation of aliphatic halides and pseudohalides with bis(catecholato)diboron (B2cat2) as the boron source is introduced. The borylation reaction is operationally simple and shows high
Alumina grafted SBA-15 sustainable bifunctional catalysts for direct cross-coupling of benzylic alcohols to diarylmethanes
Rajendran, Chandran,Satishkumar, Govindaswamy,Lang, Charlotte,Gaigneaux, Eric M.
, p. 2583 - 2592 (2020/05/14)
AlSBA-15 catalysts possessing Br?nsted acid and Lewis acid-base bifunctionalities catalyze the direct arylation of benzyl alcohols to diarylmethanes with an 85% product yield through C-O bond activation. 2 and 4wt%AlSBA-15 catalysts have been synthesised by adopting a simple and efficient post-synthetic metal implantation route. The synthesised catalysts were characterized using XRD, N2 adsorption and desorption, 27Al MAS NMR, XPS, HR-TEM, NH3 and CO2-temperature-programmed desorption (TPD) and pyridine-transmission-FTIR spectroscopy techniques to confirm the existence of Br?nsted acid and Lewis acid-base bifunctionalities. Through various control experiments, it is verified that Br?nsted acid sites activate the benzyl alcohol and Lewis base sites interact with phenylboronic acid concurrently to accomplish the coupling reaction. In the recyclability study, 4wt%AlSBA-15 preserves its activity and stability up to 5 cycles. The 4wt%AlSBA-15 catalyst unlike homogeneous catalysts does not require additives, long reaction time and expensive metals.
Selective Conversion of Benzylic Phosphates into Diarylmethanes Through Al(OTf)3-Catalyzed Friedel–Crafts-Type Benzylation
Yurino, Taiga,Hachiya, Asuka,Suzuki, Keisuke,Ohkuma, Takeshi
, p. 2225 - 2232 (2020/04/16)
Al(OTf)3 was identified as a high-performance catalyst for Friedel–Crafts-type benzylation using benzylic phosphates as electrophiles. The reaction proceeded even with 0.2 mol-% of the catalyst. A series of diarylmethanes (21 examples) was obtained in moderate to high yield. The catalyst showed unique chemoselectivity, preferentially converting the benzylic phosphate motif, even with a benzylic acetate group existed in the same molecule.
Cross coupling of benzylammonium salts with boronic acids using a well-defined N-heterocyclic carbene-palladium(ii) precatalyst
Wang, Tao,Guo, Jiarui,Wang, Xiaojuan,Guo, Han,Jia, Dingli,Wang, Hengjin,Liu, Lantao
, p. 5738 - 5741 (2019/03/02)
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. Notably, in the presence of the easily prepared and bench-stable Pd-PEPPSI precatalyst, the Csp3-N bond activation of the benzylammonium salt even proceeded smoothly in isopropanol at room temperature.
Palladium-Catalysed Cross-Coupling of Benzylammonium Salts with Boronic Acids under Mild Conditions
Türtscher, Paul L.,Davis, Holly J.,Phipps, Robert J.
, p. 793 - 803 (2017/10/07)
Herein, we give a full account of the development of the palladium-catalysed cross-coupling of benzylammonium salts with boronic acids. A range of benzylamine-derived quaternary ammonium salts can be coupled with boronic acids under relatively mild conditions. Our optimization has identified ligands that can be used to chemoselectively cross-couple at the ammonium in the presence of chlorides. We demonstrate that intramolecular palladium-catalysed C-H activation is also a viable pathway for the putative benzyl-Pd(II) intermediate obtained upon oxidative addition and have optimised this to obtain fluorene in good yield.
Transition-metal-free cross-coupling reaction of benzylic halides with arylboronic acids leading to diarylmethanes
Ueda, Mitsuhiro,Nakakoji, Daiki,Kuwahara, Yuki,Nishimura, Kota,Ryu, Ilhyong
, p. 4142 - 4144 (2016/08/24)
The cross-coupling reaction between arylboronic acids and various benzylic halides proceeded without using a transition-metal catalyst to give the corresponding diarylmethanes in moderate to good yields.
Intra- and Intermolecular Nickel-Catalyzed Reductive Cross-Electrophile Coupling Reactions of Benzylic Esters with Aryl Halides
Konev, Mikhail O.,Hanna, Luke E.,Jarvo, Elizabeth R.
supporting information, p. 6730 - 6733 (2016/06/09)
Nickel-catalyzed cross-electrophile coupling reactions of benzylic esters and aryl halides have been developed. Both inter- and intramolecular variants proceed under mild reaction conditions. A range of heterocycles and functional groups are tolerated under the reaction conditions. Additionally, the first example of a stereospecific cross-electrophile coupling of a secondary benzylic ester is described. Crossed off: Nickel-catalyzed cross-electrophile coupling reactions of benzylic esters and aryl halides have been developed. Both inter- and intramolecular variants proceed under mild reaction conditions, and a range of heterocycles and functional groups are tolerated. Additionally, the first example of a stereospecific cross-electrophile coupling of a secondary benzylic ester is described.
Ethers as hydrogen sources in BF3·OEt2 promoted reduction of diphenylmethyl alcohols, ethers and esters to hydrocarbons
Li, Jiaqiang,Liu, Qing,Shen, Hang,Huang, Ruofeng,Zhang, Xiaohui,Xiong, Yan,Chen, Changguo
, p. 85291 - 85295 (2015/11/02)
A novel ether/BF3 reductive system has been described, in which diphenylmethanols and their ether and ester derivatives are used as starting materials. Reductions are performed in ether under reflux and an argon atmosphere, and the addition of extra water is beneficial to this reduction. A series of alkanes are able to be prepared with good to excellent yields. A deuterated experiment exhibits that the reductive hydrogen is generated from ether. The mechanism is discussed in detail to explain the observed reactivity.
Ni(ii) source as a pre-catalyst for the cross-coupling of benzylic pivalates with arylboronic acids: Facile access to tri- and diarylmethanes
Chen, Qiang,Fan, Xin-Heng,Zhang, Li-Peng,Yang, Lian-Ming
, p. 15338 - 15340 (2015/02/19)
A simple and easily-used NiII complex, Ni(PPh3)2(1-naphthyl)Cl, was employed as a pre-catalyst in the Suzuki-Miyaura cross-coupling of benzylic pivalates with arylboronic acids, affording various tri- or diarylmethanes in good yields under mild conditions. This new protocol provides a cheap, convenient and practical alternative to synthesizing multiaryl methanes. This journal is
