77897-02-0Relevant articles and documents
Palladium-Catalyzed Coupling of Biphenyl-2-yl Trifluoromethanesulfonates with Dibromomethane to Access Fluorenes
Pan, Shulei,Zhang, Yanghui,Zhu, Qiongqiong
supporting information, (2022/03/27)
A facile and efficient method has been developed for the synthesis of fluorenes by Pd-catalyzed C-H alkylation of biphenyl-2-yl trifluoromethanesulfonates. The trifluoromethanesulfonates are more readily available and more environmentally benign than biphenyl iodides, and are advantageous substrates for traceless directing-groupassisted C-H activation. The reaction generates C,C-palladacycles as the key intermediates that form two C(sp2)-C(sp3) bonds through reaction with CH2Br2. The reaction tolerates various functional groups, permitting easy access to a range of fluorene derivatives.
Nickel-catalyzed methylation of aryl halides/tosylates with methyl tosylate
Wang, Jiawang,Zhao, Jianhong,Gong, Hegui
, p. 10180 - 10183 (2017/09/23)
This work describes the cross-electrophile methylation of aryl bromides and aryl tosylates with methyl tosylate. The mild reaction conditions allow effective methylation of a wide set of heteroaryl electrophiles and dimethylation of dibromoarenes.
Synthesis of 2,2′-biphenols through direct C(sp2)-H hydroxylation of [1,1′-biphenyl]-2-ols
Duan, Shitao,Xu, Yuanshuang,Zhang, Xinying,Fan, Xuesen
supporting information, p. 10529 - 10532 (2016/09/02)
A novel synthesis of diversely substituted 2,2′-biphenols through Pd(ii)-catalyzed, tBuOOH-oxidized, and hydroxyl-directed C(sp2)-H hydroxylation of [1,1′-biphenyl]-2-ols has been developed. Notably, this finding is distinct from previous reports in which [1,1′-biphenyl]-2-ols underwent an intramolecular C-H activation and C-O bond formation to afford dibenzofurans under the promotion of Pd(ii) but in the absence of tBuOOH.
Synthesis of biaryls via intramolecular free radical ipso-substitution reactions
Ujjainwalla, Feroze,Da Mata, Maria Lucília E.N.,Pennell, Andrew M.K.,Escolano, Carmen,Motherwell, William B.,Vázquez, Santiago
, p. 6701 - 6719 (2015/08/24)
A variety of functionalised biaryls and heterobiaryls are prepared by intramolecular free radical [1,5]-ipso-substitution using sulfonamide and sulfonate derived tethering chains. The overall efficiency of the process is determined by appropriately positioned substituents on the aromatic acceptor ring. The extension of the process to benzylic sulfonates and their corresponding N-methylsulfonamide alternatives as substrates in potential [1,6]-ipso-substitution reactions leads mainly to the alternative [1,7] addition products.
Nickel-catalyzed cross-coupling of anisole derivatives with trimethylaluminum through the cleavage of carbonoxygen bonds
Morioka, Toshifumi,Nishizawa, Akihiro,Nakamura, Keisuke,Tobisu, Mamoru,Chatani, Naoto
supporting information, p. 1729 - 1731 (2016/02/19)
Nickel-catalyzed cross-coupling of methoxyarenes with trimethylaluminum is described. The use of 1,3-dicyclohexylimidazol-2-ylidene as a ligand and NaO'Bu as a base promotes the methylation of anisole derivatives via the cleavage of normally unreactive aryl carbonoxygen bonds.
Synthesis of 2-Arylphenol Derivatives through a One-Pot Suzuki-Miyaura Coupling/Dehydrogenative Aromatization Sequence with Pd/C Catalysis
Kikushima, Kotaro,Nishina, Yuta
supporting information, p. 5864 - 5868 (2015/09/15)
One-pot synthesis of 2-arylphenols starting from 2-iodo-2-cyclohexen-1-one and arylboronic acids through sequential Suzuki-Miyaura coupling/dehydrogenative aromatization with Pd/C catalysis has been developed. A range of arylboronic acids serve as substrates, including those containing electron-donating or electron-withdrawing groups. Additionally, one-pot synthesis of di- or trisubstituted phenols bearing a phenyl group at the ortho position are also generated by using 2-iodo-2-cyclohexen-1-one derivatives as substrate. In the present method, commercially available and easily removable Pd/C was employed as a catalyst without any ligands. The operationally simple procedure and accessible conditions were used to provide modified phenols as the sole product in moderate to high yields.
Titanium salan catalysts for the asymmetric epoxidation of alkenes: Steric and electronic factors governing the activity and enantioselectivity
Talsi, Evgenii P.,Samsonenko, Denis G.,Bryliakov, Konstantin P.
supporting information, p. 14329 - 14335 (2015/01/09)
A new insight into the highly enantioselective (up to > 99.5% ee ) epoxidation of olefins in the presence of chiral titanium(IV) salan complexes is reported. A series of 14 chiral ligands with varying steric and electronic properties have been designed, a
Synthesis of dibenzopyranones through palladium-catalyzed directed C-H activation/carbonylation of 2-arylphenols
Luo, Shuang,Luo, Fei-Xian,Zhang, Xi-Sha,Shi, Zhang-Jie
supporting information, p. 10598 - 10601 (2013/10/21)
Dibenzopyranones were synthesized by a palladium-catalyzed phenol-directed C-H activation/carbonylation of 2-phenylphenol derivatives in the presence of CO. Pd(OAc)2 was used as a catalyst and Cu(OAc)2 as a catalytic oxidant in the presence of air. Copyright
Ruthenium-catalyzed carbonylative C-H cyclization of 2-arylphenols: A novel synthetic route to 6 H-dibenzo[b,d]pyran-6-ones
Inamoto, Kiyofumi,Kadokawa, Jun,Kondo, Yoshinori
supporting information, p. 3962 - 3965 (2013/09/02)
Catalytic carbonylative C-H cyclization of 2-arylphenols can be achieved in the presence of a ruthenium-based catalytic system. The process proceeds efficiently under balloon pressure of CO and produces variously substituted 6H-dibenzo[b,d]pyran-6-one compounds, typically in good to high yields. Functional groups such as the alkoxycarbonyl and acetyl groups as well as halogen atoms (F, Cl, and Br) are well tolerated during the reaction.
Copper-catalyzed oxidative aromatization of 2-cyclohexen-1-ones to phenols in the presence of catalytic hydrogen bromide under molecular oxygen
Kikushima, Kotaro,Nishina, Yuta
, p. 20150 - 20156 (2013/11/06)
Catalytic oxidative aromatization has been achieved using 2-cyclohexen-1-ones to obtain phenol derivatives in the presence of a catalytic amount of copper salt and aqueous HBr under molecular oxygen. The amount of HBr was successfully reduced to a catalytic quantity, and the other additive such as a ligand and an oxidant as well as inert conditions were unnecessary. Various mono-, di-, and trisubstituted phenols with substituents at the desired positions could be synthesized under cheap and simple conditions. An oxidative aromatization/bromination sequence was also demonstrated to obtain bromophenols with excess HBr. The Royal Society of Chemistry 2013.