NOBIN-based phosphoramidite and phosphorodiamiditeligands and their use in asymmetric nickel-catalysed hydrovinylation

文献信息

发布日期 2012-11-01
DOI 10.1039/C2CY20657A
影响因子 6.119
作者

Mike Schmitkamp, Walter Leitner, Giancarlo Franciò


查看原文

摘要

Phosphoramidite and P-stereogenic phosphorodiamidite ligands derived from (Sa)-2-phenylamino-2′-hydroxy-1,1′-binaphthyl (N-Ph-NOBIN) and bis(1-phenyl-ethyl)amine were synthesised, fully characterised, and the absolute configuration of the stereogenic phosphorus atoms was assigned. The phosphoramidite ligand L2 features three non-bridged substituents at phosphorus comprising the bis(1-phenylethyl)amine and two NOBIN moieties. The NOBIN units are bound to the phosphorus through the oxygen atoms with two pendant nitrogen atoms. In the Ni-catalysed hydrovinylation of styrene no conversion was observed with the phosphorodiamidites, while the phosphoramidite ligands led to active catalysts with a marked co-operative effect on selectivities. Whereas the racemic product was obtained with the (Sa,Sa,SC,SC) diastereomer, the (Sa,Sa,RC,RC) diastereomer proved to be one of the best ligands for this reaction, leading to almost perfect selectivity and ees of up to 91%.

相关文献

Indium nitride crystals with flower-like structure

Naoyuki Takahashi, Arei Niwa, Haruka Sugiura, Takato Nakamura

2003-01-14 Communication

DOI: 10.1039/B211099G

Novel intermolecular carbon radical addition to a nitrone: asymmetric synthesis of α-amino acids

Masafumi Ueda, Hideto Miyabe, Masako Teramachi, Okiko Miyata, Takeaki Naito

2003-01-14 Communication

DOI: 10.1039/B211570K

Engineering redox functions in a nucleic acid binding protein

Jon R. Wilson, Daren J. Caruana, Gianfranco Gilardi

2003-01-02 Communication

DOI: 10.1039/B209443F

A convenient palladium-catalyzed aerobic oxidation of alcohols at room temperature

Mitchell J. Schultz, Candice C. Park, Matthew S. Sigman

2002-11-14 Communication

DOI: 10.1039/B209344H

Charge-transfer band shifts in iron(iii) hexacyanoferrate(ii) by electro-intercalated cationsvia ground state-energy/lattice-energy link

David R. Rosseinsky, Xiao Zhang, Hongjin Jiang, Jian Wei Chai

2002-11-08 Communication

DOI: 10.1039/B209708G

1,3-Dimethylimidazolium-2-carboxylate: the unexpected synthesis of an ionic liquid precursor and carbene-CO2 adduct

John D. Holbrey, W. Matthew Reichert, Igor Tkatchenko, Ezzedine Bouajila, Olaf Walter, Immacolata Tommasi, Robin D. Rogers

2002-12-05 Communication

DOI: 10.1039/B211519K

Novel bis-acac-O,O–Ir(iii) catalyst for anti-Markovnikov, hydroarylation of olefins operates by arene CH activation

Roy A. Periana, Xiang Y. Liu, Gaurav Bhalla

2002-11-13 Communication

DOI: 10.1039/B208680H

Photochemistry of single wall carbon nanotubes embedded in a mesoporous silica matrix

Mercedes Álvaro, Pedro Atienzar, José L. Bourdelande, Hermenegildo García

2002-11-13 Communication

DOI: 10.1039/B209225P

Formation and structural observation of cesium encapsulated single-walled carbon nanotubes

Goo-Hwan Jeong, Rikizo Hatakeyama, Takamichi Hirata, Kazuyuki Tohji, Kenichi Motomiya, Toshie Yaguchi, Yoshiyuki Kawazoe

2002-12-05 Communication

DOI: 10.1039/B210079G

您可能还喜欢

化合物问答

如何处理含有8-氯咪唑并[1,2-A]吡嗪(CAS号:69214-33-1)的废料?

处理含有8-氯咪唑并[1,2-A]吡嗪的废料时,应首先将其收集并进行化学回收或降解。如果无法回收,需采用安全的化学处理方法,如中和、氧化还原或沉淀。处理过程中需...

69214-33-18-chloroimidazo[1,2-...
化合物问答

Calhex 231 hydrochloride(CAS号:2387505-78-2)适用哪些法规指南?

Calhex 231 hydrochloride 需要遵循《全球化学品统一分类和标签制度》(GHS)的分类和标签要求,以及欧盟的《化学品注册、评估、授权和限制条...

2387505-78-24-Chloro-N-[(1S,2S)-...
化合物问答

11-Beta,17-alpha,21-三羟基-5-beta-孕烯-3,20-二酮(CAS号:1482-50-4)的物理化学性质是什么?

11-Beta,17-alpha,21-三羟基-5-beta-孕烯-3,20-二酮是一种无色结晶性粉末,分子量为372.45 g/mol。该化合物在水中的溶解度...

1482-50-45β-Dihydrocortisol
化合物问答

处理5-异丙基-1,3,4-恶二唑-2-羧酸(CAS号:944907-13-5)时应注意哪些实验室安全事项?

处理5-异丙基-1,3,4-恶二唑-2-羧酸时应注意以下安全事项:穿戴适当的个人防护装备,包括实验室外套、手套和护目镜;操作应在通风橱中进行,以减少吸入或接触有...

944907-13-55-Isopropyl-1,3,4-ox...
化合物问答

benzyl 3-bromopropanoate(CAS号:90841-55-7)安全吗?

Benzyl 3-bromopropanoate属于有毒物质,吸入、摄入或皮肤接触均可能对人体造成伤害。操作时应佩戴防护眼镜、口罩和手套,避免吸入蒸汽和直接接触...

90841-55-7Benzyl 3-bromopropan...
化合物问答

什么是(R)-N-苄氧羰基-3,4-二氢-1H-异喹啉羧酸(CAS号:151004-88-5)?

(R)-N-苄氧羰基-3,4-二氢-1H-异喹啉羧酸是一种含有苄氧羰基和异喹啉环结构的化合物,分子式为C17H15NO3。它是一种有机化合物,具有一定的生物活性...

151004-88-5(1R)-2-[(Benzyloxy)c...
化合物问答

在合成中是否有1-苄基吡啶嗡-3-羧酸盐(CAS号:15990-43-9)的替代品?

可以考虑使用1-苄基吡啶-3-羧酸盐作为1-苄基吡啶嗡-3-羧酸盐的替代品。此外,还可以探索其他类似物,如1-苄基吡啶-3-氨基甲酸酯等。具体的替代品选择需根据...

15990-43-91-Benzyl-3-pyridiniu...
化合物问答

(2,6-二甲基吡啶-3-基)甲醇(CAS号:582303-10-4)安全吗?

(2,6-二甲基吡啶-3-基)甲醇在使用时需注意安全,应避免吸入其蒸汽,接触皮肤和眼睛。操作应在通风良好的环境中进行,佩戴适当的个人防护装备。

582303-10-4(2,6-Dimethyl-3-pyri...
化合物问答

5-溴-2-乙烯基吡啶(CAS号:226883-52-9)的物理化学性质是什么?

5-溴-2-乙烯基吡啶是一种有机化合物,外观为白色固体,具有良好的结晶性。分子量约为190.03 g/mol。它的溶解性在水中较差,但在有机溶剂如二氯甲烷、甲醇...

226883-52-95-Bromo-2-vinylpyrid...
化合物问答

2-羟基-3-硝基-5-甲基吡啶(CAS号:7464-14-4)应用于哪些行业?

2-羟基-3-硝基-5-甲基吡啶主要应用于医药、聚合物和半导体行业。在医药领域,它可以用作合成其他药物的中间体。在聚合物领域,它可以作为功能性单体参与聚合反应,...

7464-14-45-Methyl-3-nitro-2(1...

来源期刊

Catalysis Science & Technology

Catalysis Science & Technology
CiteScore: 5.91
自引率: 4.5%
年发文量: 600

Catalysis Science & Technology is committed to publishing research reporting high-quality, cutting-edge developments across the catalysis community at large. The journal places equal focus on publications from the heterogeneous, homogeneous, thermo-, electro-, photo-, organo- and biocatalysis communities. Works published in the journal feature a balanced mix of fundamental, technology-oriented, experimental, computational, digital and data-driven original research, thus appealing to catalysis practitioners in both academic and industrial environments. Original research articles published in the journal must demonstrate new catalytic discoveries and/or methodological advances that represent a significant advance on previously published work, from the molecular to the process scales. We welcome rigorous research in a wide range of timely or emerging applications related to the environment, health, energy and materials. Catalysis Science & Technology publishes Communications, Articles, Reviews and Perspectives. More details regarding manuscript types may be found in the Information for Authors section.

推荐供应商

免责声明
本页面提供的学术期刊信息仅供参考和研究使用。我们与任何期刊出版商均无关联,也不处理投稿事宜。如有投稿相关咨询,请直接联系相关期刊出版商。
如发现页面信息有误,请发送邮件至 support@chemtradehub.com 联系我们。我们将及时核实并处理您的问题。