18110-71-9Relevant academic research and scientific papers
Nickel-Catalyzed Ortho-Arylation of Unactivated (Hetero)aryl C-H Bonds with Arylsilanes Using a Removable Auxiliary
Zhao, Sheng,Liu, Bin,Zhan, Bei-Bei,Zhang, Wei-Dong,Shi, Bing-Feng
, p. 4586 - 4589 (2016)
Ni(II)-catalyzed ortho-arylation of aromatic and heteroaromatic carboxamides with triethoxy(aryl)silanes assisted by a removable bidentate auxiliary is reported. This transformation features a broad substrate scope, good functional group tolerance, and co
Palladium-catalyzed intramolecular aromatic C-H acylation of 2-arylbenzoyl fluorides
Hayakawa, Kazuki,Ikai, Kana,Ogiwara, Yohei,Sakai, Norio,Sakurai, Yuka
, p. 1882 - 1893 (2021/08/13)
The catalytic intramolecular cyclization of acyl fluorides using a Pd(OAc)2/PCy3 system is described. A wide range of 2-arylbenzoyl fluoride derivatives can be used as fluorenone precursors and the reaction proceeds via an intramolecular coupling between aromatic C-H bonds with acyl C-F bonds. The reaction can be applied to the synthesis of indenofluorenedione derivatives and to the construction of other molecules with fivemembered rings.
Transition-Metal-Free Synthesis of Phenanthridinones through Visible-Light-Driven Oxidative C–H Amidation
Usami, Kaoru,Yamaguchi, Eiji,Tada, Norihiro,Itoh, Akichika
, p. 1496 - 1504 (2019/06/27)
The treatment of N-aryl biphenylcarboxamide, 1-chloroanthraquinone (1-Cl-AQN) catalyst, and K2CO3 in CHCl3 under visible light irradiation affords phenanthridinone via radical cyclization. This reaction proceeds under transition-metal-free condition, room temperature, and direct C–H amidation. Mechanistic studies indicate that amidyl radical generation proceeds by visible light induced proton coupled electron transfer (PCET) from N–H bond of the amide.
Visible-Light-Induced Arene C(sp 2)-H Lactonization Promoted by DDQ and tert -Butyl Nitrite
Chen, Bajin,Hu, Baoxiang,Hu, Xinquan,Jin, Liqun,Li, Meichao,Shen, Zhenlu,Sun, Nan,Wang, Shengpeng,Wang, Yiqing
supporting information, p. 261 - 266 (2020/02/18)
A visible-light photocatalytic aerobic oxidative lactonization of arene C(sp 2)-H bonds proceeds in the presence of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and tert -butyl nitrite (TBN). Under the optimized conditions, a range of 2-arylbenzoic acids is converted into the corresponding benzocoumarin derivatives in moderate to excellent yields. This method is characterized by its atom economy, mild reaction conditions, the use of a green oxidant and metal-free catalysis.
Facile preparation of 3,4-benzocoumarins from 2-arylbenzoic acids with NCS and NAI
Nakamura, Momoko,Togo, Hideo
, (2020/09/15)
– Treatment of 2-arylbenzoic acids with N-chlorosuccinimide (NCS) and NaI at 70 °C under fluorescent lighting condition gave the corresponding 3,4-benzocoumarins in good yields under transition-metal-free condition. It was found that the reactivity of NCS
Vitamin Catalysis: Direct, Photocatalytic Synthesis of Benzocoumarins via (-)-Riboflavin-Mediated Electron Transfer
Morack, Tobias,Metternich, Jan B.,Gilmour, Ryan
supporting information, p. 1316 - 1319 (2018/03/09)
An operationally simple protocol is disclosed to facilitate entry to benzo-3,4-coumarins directly from biaryl carboxylic acids without the need for substrate prefunctionalization. Complementary to classic lactonization strategies, this disconnection relies on the oxidation competence of photoactivated (-)-riboflavin (vitamin B2) to generate the heterocyclic core via photoinduced single electron transfer. Collectively, the inexpensive nature of the catalyst, ease of execution, and absence of external metal additives are a convincing endorsement for the incorporation of simple vitamins in contemporary catalysis.
Oxidant-Free C(sp2)-H Functionalization/C-O Bond Formation: A Kolbe Oxidative Cyclization Process
Zhang, Lei,Zhang, Zhenxing,Hong, Junting,Yu, Jian,Zhang, Jianning,Mo, Fanyang
, p. 3200 - 3207 (2018/03/25)
An anodic oxidation/cyclization of 2-arylbenzoic acids for the synthesis of dibenzopyranones has been developed. The reaction proceeds at room temperature with no oxidant or electrolyte required and exhibits a high atom economy with H2 being th
Palladium-Catalyzed, N-(2-Aminophenyl)acetamide-Assisted Ortho-Arylation of Substituted Benzamides: Application to the Synthesis of Urolithins B, M6, and M7
Reddy, M. Damoder,Blanton, Alexandra N.,Watkins, E. Blake
, p. 5080 - 5095 (2017/05/24)
Pd-catalyzed, selective, monoarylation of ortho-C-H bonds of various benzamides with aryl/heteroaryl iodides has been realized using N-(2-aminophenyl)acetamide (APA) as a new bidentate directing group for the first time. The reaction was tolerant of a wid
Ruthenium(II)-catalyzed C-H functionalizations on benzoic acids with aryl, alkenyl and alkynyl halides by weak-: O -coordination
Mei, Ruhuai,Zhu, Cuiju,Ackermann, Lutz
supporting information, p. 13171 - 13174 (2016/11/09)
C-H arylations of weakly coordinating benzoic acids were achieved by versatile ruthenium(ii) catalysis with ample substrate scope. Thus, user-friendly ruthenium(ii) biscarboxylate complexes modified with tricyclohexylphosphine enabled C-H functionalizations with aryl electrophiles. The unique versatility of the ruthenium(ii) catalysis manifold was reflected by facilitating effective C-H activations with aryl, alkenyl and alkynyl halides.
Room-temperature cobalt-catalyzed arylation of aromatic acids: overriding the ortho-selectivity via the oxidative assembly of carboxylate and aryl titanate reagents using oxygen
Liu, Kun-Ming,Zhang, Rui,Duan, Xin-Fang
supporting information, p. 1593 - 1598 (2016/02/09)
A room temperature phosphine or NHC ligand-free cobalt-catalyzed arylation of (hetero)aromatic acids has been developed. It involves an oxidative cross-coupling between carboxylate and aryl titanate reagents using oxygen as an oxidant, and the arylation at the position ortho, meta and para to the carboxylic acid group could all be achieved. As application, various (hetero)aromatic acids including xenalipin, tafamidis and the key intermediate for a cardioprotective compound have been efficiently synthesized.
