32832-95-4Relevant academic research and scientific papers
Desulfurative Ni-Catalyzed Reductive Cross-Coupling of Benzyl Mercaptans/Mercaptoacetates with Aryl Halides
Chan, Cheng-Lin,Hsu, Che-Ming,Lee, Shao-Chi,Li, Li-Yun,Liao, Hsuan-Hung,Mi?oza, Shinje,Tsai, Hao-En,Tsai, Zong-Nan,Tsao, Yong-Ting
, (2022/02/07)
The C-S activation and sulfur removal from native thiols is challenging, which limits their application as feedstock materials in organic synthesis despite their natural abundance. Herein, we introduce a per-/polyfluoroaryl moiety, which serves as a redox-active scaffold, into sp3-hybridized thiols to activate the C-S bond. Using a Ni catalyst with MgBr2 as an additive, the S group can be removed to yield an aliphatic radical that can react with an aryl halide in a reductive cross-coupling.
Regiodivergent CDC reactions of aromatic aldehydes with unactivated arenes controlled by transient directing strategy
Bai, Chaolumen,Baiyin, Menghe,Bao, Agula,Bao, Yong-Sheng,Chao, Bao,Liu, Dan,Muschin, Tegshi
supporting information, p. 11229 - 11232 (2021/11/03)
The regiodivergent catalytic dehydrogenative cross-coupling reactions at both sp2and sp3hybridized carbons of aromatic compounds are particularly challenging. Herein, we report the finding of transient directing group controlled regiodivergent C(sp3)-C(sp2) and C(sp2)-C(sp2) cross-coupling in theo-methyl benzaldehyde frameworks. Catalyzed by palladium, using K2S2O8or [F+] reagents as by-standing oxidants and unactivated arenes as substrates/solvents, various benzyl benzaldehydes or phenyl benzaldehydes were prepared. A mechanism study indicated that the regiospecificity is dominated by the [5,6]-fused palladacycle or [6,5]-fused palladacycle intermediates, which are generated from Pd-chelation with specified transient directing groups and further C-H activations.
Palladium-catalyzed benzylic C(sp3)–H arylation of o-alkylbenzaldehydes
Lei, Lan,Wu, Ping,Liu, Zhuqing,Lou, Jiang
supporting information, (2021/02/16)
The palladium-catalyzed benzylic C(sp3)–H arylation of o-alkylbenzaldehyde derivatives was achieved utilizing 2-dimethylaminoethylamine as a novel transient directing group. The γ-C(sp3)–H arylation reaction efficiently afforded a variety of arylated o-alkylbenzaldehydes and polycyclic aromatic hydrocarbons (PAHs) in one pot, exhibiting high functional group tolerance with broad substrate scope. The aliphatic diamine auxiliary represents a simple, inexpensive, readily available, and removable directing group for C–H activation. The resultant o-benzylbenzaldehyde products could be diversely transformed into potentially important synthetic intermediates under mild conditions.
Nano palladium catalyzed C(sp3)[sbnd]H bonds arylation by a transient directing strategy
Chen, Jianxia,Bai, Chaolumen,Ma, Hongpeng,Liu, Dan,Bao, Yong-Sheng
supporting information, p. 465 - 469 (2020/03/19)
Reported herein is the first example of heterogeneous palladium catalyzed C(sp3)-H bonds arylation by a transient-ligand-directed strategy. Using supported palladium (metallic state) nanopariticles as catalyst, a wide range of aryl iodides undergo the coupling with various o-methylbenzaldehyde derivatives to assemble a library of highly selective and functionalized o-benzylbenzaldehydes. The stability of the catalyst was easily recovered four runs without significant loss of activity. The XPS analysis of the catalyst before and after reaction indicated that the reaction might be carried out by a catalytic cycle starting with Pd0.
Synthesis of Benzoazepine Derivatives via Azide Rearrangement and Evaluation of Their Antianxiety Activities
Lapmanee, Sarawut,Palavong, Nitwaree,Reamtong, Onrapak,Ruchirawat, Somsak,Thongsornkleeb, Charnsak,Tummatorn, Jumreang
supporting information, p. 1449 - 1458 (2021/09/13)
A new synthetic method for the construction of benzoazepine analogues has been developed employing ortho-arylmethylbenzyl azide derivatives as precursors using an azide rearrangement reaction. In this work, 14 benzoazepine compounds were successfully synthesized in moderate to excellent yields. All synthetic benzoazepines were evaluated for their cytotoxicity against normal human kidney cell line (HEK cell). The results showed that compound 18c had the lowest cytotoxicity (IC50 = 65.68 μM) among tested compounds, which was comparable with the antianxiety drug diazepam (IC50 = 87.90 μM). Based on the cytotoxicity results, five benzoazepine analogues (compounds 18c, 18h, 18j, 18n, and 18p) were selected to determine the antianxiety effect on stressed rats using elevated plus maze (EPM) and open field test (OFT) methods. Interestingly, compound 18c showed better anxiolytic activity than diazepam without a sedative effect by showing superior hyperlocomotor activity. Therefore, this discovery could pave the way for drug development to treat patients with anxiety disorder.
Ligand-Controlled Direct γ-C?H Arylation of Aldehydes
Ge, Haibo,Lawrence, Brianna,Li, Bijin,Li, Guigen
supporting information, p. 3078 - 3082 (2020/02/05)
The first example of PdII-catalyzed γ-C(sp3)?H functionalization of aliphatic and benzoheteroaryl aldehydes has been developed using a transient ligand and an external ligand, concurrently. A wide array of γ-arylated aldehydes were readily accessed without preinstalling internal directing groups. The catalytic mechanism was studied by performing deuterium-labelling experiments, which indicated that the γ-C(sp3)?H bond cleavage is the rate-limiting step during the reaction process. This reaction could be performed on a gram scale, and also demonstrated its potential application in the synthesis of new mechanofluorochromic materials with blue-shifted mechanochromic properties.
Palladium-Catalyzed Three-Component Coupling Reaction of o-Bromobenzaldehyde, N-Tosylhydrazone, and Methanol
Zhu, Lei,Ren, Xiaojian,Yu, Yinghua,Ou, Pengcheng,Wang, Zhi-Xiang,Huang, Xueliang
, p. 2087 - 2092 (2020/03/04)
A ligand-controlled palladium-catalyzed three-component reaction of o-bromobenzaldehyde, N-tosylhydrazone, and methanol is described. This reaction uses readily available compounds as starting materials while displaying a broad substrate scope and good functional group compatibility.
Semicarbazide: A Transient Directing Group for C(sp3)?H Arylation of 2-Methylbenzaldehydes
Wen, Fei,Li, Zheng
supporting information, p. 133 - 138 (2019/11/28)
Semicarbazide as an effective transient directing group for C(sp3)?H arylation of 2-methylbenzaldehydes is described. Various substituted 2-benzylbenzaldehydes are efficiently synthesized by this strategy. The salient features of this protocol are the use of inexpensive transient directing group, wide scope of substrates with good functional group compatibility, up to 98% yield, and applicability to gram scale. (Figure presented.).
Glycinamide hydrochloride as a transient directing group: Synthesis of 2-benzylbenzaldehydes by C(sp3)?H arylation
Wen, Fei,Li, Zheng
supporting information, p. 3462 - 3474 (2020/08/10)
Glycinamide hydrochloride as an inexpensive and commercially available transient directing group for the C(sp3)?H arylation of 2-methylbenzaldehydes is described. A series of practical 2-benzylbenzaldehydes bearing various functional groups are efficiently synthesized in satisfactory yield by this strategy. This method can also be extended to gram scale.
Synthesis method of 2-benzylbenzaldehyde derivative
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Paragraph 0018-0019; 0025-0031, (2020/12/15)
The invention discloses a synthesis method of an important organic synthesis intermediate 2-benzyl benzaldehyde derivative for constructing bioactive molecules. The synthesis of the 2-benzyl benzaldehyde is realized in one step by taking cheap and easily
