4.5 Article

Revisiting the Hirao cross-coupling: improved synthesis of aryl and heteroaryl phosphonates

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JOURNAL OF ORGANOMETALLIC CHEMISTRY
卷 693, 期 19, 页码 3171-3178

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ELSEVIER SCIENCE SA
DOI: 10.1016/j.jorganchem.2008.07.020

关键词

cross-coupling; phosphorus; palladium; heterocycles; aryl halides

资金

  1. National Institute of General Medical Sciences/NIH [1R01 GM067610]
  2. TCU-SERC

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The palladium-catalyzed cross-coupling of dialkylphosphite with aromatic electrophiles (Hirao coupling) was re-investigated. Some limitations in terms of palladium loadings and substrate reactivity are alleviated with the use of Pd(OAc)(2) complexed to 1,1'-bis(diphenylphosphino) ferrocene (dppf) as a ligand. Various aryl and heteroaryl halides are employed to deliver both known and novel substituted phosphonates. The first examples of aryl chloride couplings are also reported. (C) 2008 Elsevier B.V. All rights reserved.

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Lima, Li Lin, Tong Ling, Yuchen Liu, Zhonghua Liu, Yao Lu, Fok M. Lum, Hang Luo, Jatin Machhi, Angus Macleod, Isaac Macwan, Hanumantha R. Madala, Nima Madani, Nicola de Maio, Kalina Makowiecki, Daniel J. Mallinson, Ruta Margelyte, Caracausi Maria, Y. Markonis, Luca Marsili, Suzanne Mavoa, Lorna McWilliams, Moa Megersa, Caetano S. M. Mendes, Julia Menichetti, Rebecca Mercieca-Bebber, Jack J. Miller, David-Paul M. Minde, Alexander Minges, Eleanor Mishra, Virendra R. Mishra, Carly Moores, Nicola Morrice, Alexander E. Moskalensky, Nicolo Navarin, Edessa Negera, Philippe Nolet, Ana Nordberg, Rickard Norden, Jessica P. Nowicki, Nelly Olova, Pawel Olszewski, Robert Onzima, Chih-Long Pan, Charny Park, Dong Ik Park, Seyoung Park, Chandrashekhar D. Patil, Sansoa A. Pedro, Samuel R. Perry, Jessica Peter, Brent M. Peterson, Andrea Pezzuolo, Ilya Pozdnyakov, Siyu Qian, Lei Qin, Ali Rafe, Ishier Raote, Ali Raza, Henrike Rebl, Osama Refai, Tim Regan, Tambi Richa, Mark F. Richardson, K. R. Robinson, Luca Rossoni, Romain Rouet, Soroush Safaei, Pierre H. H. Schneeberger, Daniela Schwotzer, Agata Sebastian, Jennifer Selinski, Stefanie Seltmann, Feng Sha, Nir Shalev, Jin-Long Shang, Josef Singer, Mandeep Singh, Taylor Smith, Emma Solomon-Moore, Lijuan Song, Samuele Soraggi, Ryan Stanley, Nico Steckhan, Frederic Strobl, Lorenzo Subissi, Irwan Supriyanto, Chinmay R. Surve, Tomo Suzuki, Caitlin Syme, Karl Sorelius, Young Tang, Marwa Tantawy, Sumudu Tennakoon, Serafino Teseo, Christine Toelzer, Nikola Tomov, Miguel Tovar, Linh Tran, Sushil Tripathi, Anil M. Tuladhar, Azubuike C. Ukubuiwe, Carolina O. L. Ung, Kaspar Valgepea, Hamid Vatanparast, Arnau Vidal, Fang Wang, Qing Wang, Ricky Watari, Rebecca Webster, Ruth Webster, Junnian Wei, David Wibowo, Tanja S. H. Wingenbach, Rose M. Xavier, Shumin Xiao, Peng Xiong, Shicai Xu, Shilin Xu, Ruifeng Yao, Wen Yao, Qinan Yin, Yongbo Yu, Masayoshi Zaitsu, Zian Zeineb, Xiao-Yong Zhan, Jilei Zhang, Rongqiang Zhang, Wei Zhang, Xianglilan Zhang, Shan Zheng, Bailing Zhou, Xiaoyan Zhou, Haroon Ahmad, Sayo A. Akinwumi, Gregory F. Albery, Ahmed Alhowimel, Junaid Ali, Mansour Alshehri, Mohammed Alsuhaibani, Andrey Anikin, Samuel O. Azubuike, Anders Bach-Mortensen, Lior Baltiansky, Martin Bartas, Kiflemariam Y. Belachew, Vivek Bhardwaj, Karin Binder, Nicholas S. Bland, Michael Boah, Benjamin Bullen, Giovanna E. Calabro, Tiffany J. Callahan, Bing Cao, Kelsey Chalmers, Wei Chang, Zhengping Che, Andrew T. Y. Chen, Haimin Chen, Huaming Chen, Youning Chen, Zhao Chen, YoungRok Choi, Mohiuddin A. K. Chowdhury, Martin R. Christensen, Robert S. C. Cooke, Marzia Cottini, Natalie V. Covington, Catriona Cunningham, Julien Delarocque, Lucie Devos, Aurup R. Dhar, Ke-Feng Ding, Kexian Dong, Zheng Dong, Niklas Dreyer, Chelsea Ekstrand, Tanguy Fardet, Berhanu E. Feleke, Thomas Feurer, Angela Freitas, Tian Gao, N. G. Asefa, Francesco Giganti, Piotr Grabowski, Jose R. Guerra-Mora, Chengying Guo, Xinyi Guo, Himanshu Gupta, Shuonan He, Marloes Heijne, Stephanie Heinemann, Alexander Hogrebe, Zhengping Huang, Sophinese Iskander-Rizk, Lavanya M. Iyer, Yasmin Jahan, Ameh S. James, Emmanuel Joel, Bastian Joffroy, Clara Jegousse, George Kambondo, Priyanka Karnati, Cihan Kaya, An Ke, Daniel Kelly, Rob Kickert, Peter E. Kidibule, Jennifer P. Kieselmann, Hyeon J. Kim, Takeshi Kitazawa, Aniek Lamberts, You Li, Huakang Liang, Sabrina N. Linn, Thomas Litfin, Wang Liusuo, Vasiliki Lygirou, Ajay K. Mahato, Zhi-Ming Mai, Rupert W. Major, Samira Mali, Panagiotis Mallis, Wenzhi Mao, Wenzhi Mao, Katie Marvin-Dowle, Katie Marvin-Dowle, Leanda D. Mason, Ben Merideth, Maria J. Merino-Plaza, Britt Merlaen, Rossella Messina, Anand K. Mishra, Junaid Muhammad, Conrad Musinguzi, Afroditi Nanou, Amreen Naqash, Joe T. Nguyen, Thi T. H. Nguyen, Duan Ni, Nida, Shirli Notcovich, Barnabas Ohst, Quinn R. Ollivier, Daniel F. Osses, Xiangda Peng, Arnoud Plantinga, Michael Pulia, Muhammad Rafiq, Ayush Raman, Delphine Raucher-Chene, Rafal Rawski, Asit Ray, Lubna A. Razak, Kevin Rudolf, Peter Rusch, Margaux L. Sadoine, Axel Schmidt, Roey Schurr, Stephen Searles, Saurab Sharma, Barry Sheehan, Chunhu Shi, Belal Shohayeb, Andrew Sommerlad, Jan Strehlow, Xianbao Sun, Raghav Sundar, Ghazaleh Taherzadeh, Nur D. M. Tahir, Jun Tang, Jean Testa, Zhiqi Tian, Qian Tingting, Geert P. Verheijen, Casey Vickstrom, Teng Wang, Xiaomin Wang, Zhenxing Wang, Pan Wei, Alex Wilson, Wyart, Abdul-Amir Yassine, Abbas Yousefzadeh, Asma Zare, Zhen Zeng, Chengrong Zhang, Haowen Zhang, Linxing Zhang, Tongchuan Zhang, Weijia Zhang, Zhe Zhang, Jianyu Zhou, Dongjie Zhu, Vincenzo Adamo, Adebolajo A. Adeyemo, Maria Aggelidou, Adi M. Al-Owaifeer, Arwa Z. Al-Riyami, Saeed K. Alzghari, Vibeke Andersen, Kathryn Angus, Muhammad Asaduzzaman, Hadi Asady, Dai Ato, Xiaoyong Bai, Rebecca L. Baines, Maghan Ballantyne, Bo Ban, Jill Beck, Walid Ben-Nafa, Emma Black, Antoine Blancher, Ron Blankstein, Neil Bodagh, Paulo A. V. Borges, Anastasia Brooks, Josue Brox-Ponce, Arturo Brunetti, Colin D. Canham, Piero Carninci, Richard Carvajal, Shun C. Chang, Jie Chao, Pranab Chatterjee, He Chen, Yi-Chun Chen, Adnan K. Chhatriwalla, Ibrahim Chikowe, Trees-Juen Chuang, Rosane G. Collevatti, Diego A. Valera-Cornejo, Ana Cuenda, Myriam Dao, Delphine Dauga, Zaian Deng, Kiran Devkota, Lisa V. Doan, Yaser H. A. Elewa, Dongsheng Fan, Mohammed Faruk, Shi Feifei, Trevor S. Ferguson, Francesco Fleres, Emma J. Foster, C. Stephen Foster, Tzvi Furer, Yibo Gao, Enid J. Garcia-Rivera, Adi Gazdar, Ronald B. George, Sayantan Ghosh, Elena Gianchecchi, Joshua M. Gleason, Allan Hackshaw, Adam Hall, Richard Hall, Paul Harper, William E. Hogg, Guangqun Huang, Kylie E. Hunter, Adriaan P. IJzerman, Carlos Jesus, Gao Jian, James S. Lewis, Souha S. Kanj, Harsheen Kaur, Shona Kelly, Fayez Kheir, V. S. Kichatova, Musa Kiyani, Reinhild Klein, Tom Kovesi, Jennifer L. Kraschnewski, Addanki P. Kumar, Dmitry Labutin, Alejandro Lazo-Langner, Guy Leclercq, Maoteng Li, Qingchun Li, Tangliang Li, Yongzhe Li, Wei-Ting Liao, Zheng-yin Liao, Jessica Lin, J. Lizer, Giambattista Lobreglio, Cher Lowies, Cheng Lu, Haroon Majeed, Adam Martin, Luis Martinez-Sobrido, Edwin Meresh, Marianne Middelveen, Alireza Mohebbi, Jorge Mota, Zahra Mozaheb, Ley Muyaya, Amar Nandhakumar, Sheryl H. X. Ng, Monther Obeidat, Deog-Hwan Oh, Mohammed Owais, Pia Pace-Asciak, Ajay Panwar, Caroline Park, Chris Patterson, Felipe Penagos-Tabaree, Paolo T. Pianosi, Valentina Pinzi, Clare Pridans, Anna Psaroulaki, Ravi Kumar Pujala, Leonardo Pulido-Arjona, Peng-Fei Qi, Proton Rahman, Nayanjot K. Rai, Tienush Rassaf, Julie Refardt, Walter Ricciardi, Olaf Riess, Alexandros Rovas, Frank M. Sacks, Sherif Saleh, Christopher Sampson, Axel Schmutz, Robert Sepanski, Neeraj Sharma, Manisha Singh, Paul Spearman, Mehala Subramaniapillai, Ritu Swali, Cher M. Tan, Juan I. Tellechea, Lisa-Marie Thomas, Xin Tong, Ralf Veys, Veronica Vitriol, Horng-Dar Wang, Jinhui Wang, Jiucun Wang, Jason Waugh, S. A. Webb, Brendan A. Williams, Alan D. Workman, Tingxiu Xiang, Li-Xin Xie, Jun Xu, Taosheng Xu, Chongjun Yang, Jihoon G. Yoon, Christina M. Yuan, Arno Zaritsky, Yao Zhang, Haochen Zhao, Hannah Zuckerman, Ran Lyu, Wayne Pullan, Yaoqi Zhou

DATABASE-THE JOURNAL OF BIOLOGICAL DATABASES AND CURATION (2019)

Article Medicine, General & Internal

The Road to a Hypoglycemic Care Model

Markus Moore, Saeed K. Alzghari

CUREUS JOURNAL OF MEDICAL SCIENCE (2019)

Article Medicine, General & Internal

Pain Perception and the Opioid Receptor Delta 1

Adam T. Hilgemeier, David M. Serna, Tarak P. Patel, Kerry Anne Rambaran, Zubair M. Amin, Jie An, Saeed K. Alzghari

CUREUS JOURNAL OF MEDICAL SCIENCE (2018)

Article Medicine, General & Internal

Evaluation of Factors which Influence Mortality in Gram-positive Bacteremia in Hemodialysis Patients

Kerry Anne Rambaran, Saeed K. Alzghari, Charles F. Seifert

CUREUS JOURNAL OF MEDICAL SCIENCE (2018)

Review Medicine, General & Internal

A Review of the Opioid Analgesic Benzhydrocodone-Acetaminophen

Ahmaya A. Mustafa, Robin Rajan, Jennifer D. Suarez, Saeed K. Alzghari

CUREUS JOURNAL OF MEDICAL SCIENCE (2018)

Article Medicine, General & Internal

An Unnecessary Pain: Using Pharmacogenetics for Statin-related Skeletal Muscle Toxicity

Saeed K. Alzghari

CUREUS JOURNAL OF MEDICAL SCIENCE (2018)

Article Medicine, General & Internal

The Relationship of UGT2B15 Pharmacogenetics and Lorazepam for Anxiety

Nathan R. Ching, Amna K. Alzghari, Saeed K. Alzghari

CUREUS JOURNAL OF MEDICAL SCIENCE (2018)

Article Chemistry, Inorganic & Nuclear

Synthesis of amine-bridged bis(phenolate) rare-earth metal alkoxides and their catalytic performance for the polymerization of trimethylene carbonate and L-lactide

Guojun Hu, Ziyue Deng, Yanwei Wang, Dan Yuan, Yong Zhang, Yingming Yao

Summary: A series of rare-earth metal complexes were synthesized and used as efficient initiators for the polymerization of trimethylene carbonate (TMC) and (L)-lactide ((L)-LA).

JOURNAL OF ORGANOMETALLIC CHEMISTRY (2024)

Article Chemistry, Inorganic & Nuclear

Platinated azulenes: Structures and electronic spectroscopy

Van Ha Nguyen, John H. K. Yip

Summary: In this study, eight PtII-azulene complexes were synthesized to investigate the effect of metalation on the electronic structures, spectroscopy, and luminescence of organic chromophores. The results showed that the attachment of Pt substituents to azulene affected the HOMOs, LUMOs, and luminescence properties. The study provides insights into the role of metalation in modifying the properties of organic chromophores.

JOURNAL OF ORGANOMETALLIC CHEMISTRY (2024)

Article Chemistry, Inorganic & Nuclear

Phosphine oxide donor-based dinuclear rhenium(I) metallocycles

Moon Kedia, Virender Singh, Bhaskaran Shankar, Malaichamy Sathiyendiran

Summary: This study synthesized two types of neutral binuclear metallocycles using a one-pot solvothermal method and characterized their structures. The analysis revealed that these complexes adopt a binuclear heteroleptic cyclic architecture and belong to phosphine oxide donor (P=O)-based supramolecular coordination cyclic complexes.

JOURNAL OF ORGANOMETALLIC CHEMISTRY (2024)

Article Chemistry, Inorganic & Nuclear

Al- driven deoxydehydration (DODH) of glycols in the presence of pincer type mo-catalyst

Radhey S. Srivastava

Summary: This study demonstrates the effectiveness of zero-valent elements as reductants for the deoxydehydration reaction of polyols catalyzed by ONO-pincer ligated molybdenum dioxo. The insolubility and easy separability of the reductants and their oxidized products during the reaction are emphasized. Additionally, the choice of ligand has an impact on the catalytic performance of the reaction.

JOURNAL OF ORGANOMETALLIC CHEMISTRY (2024)

Article Chemistry, Inorganic & Nuclear

New ruthenium/phosphino carbazole systems for selective preparation of alcohols under hydroformylation conditions

Hao Zhou, Yajun Sun, Li Deng, Weiran Yang, Yuehui Li

Summary: Efficient Ru-catalyzed hydrogenation of aldehydes was achieved using carbazole-derived phosphine ligands, with the crucial role of N-H moiety in promoting the catalytic reaction. The method was successfully applied in the Co/Ru-catalyzed hydroformylation process, resulting in the production of long-chain alcohols with excellent yields.

JOURNAL OF ORGANOMETALLIC CHEMISTRY (2024)

Article Chemistry, Inorganic & Nuclear

A theoretical study of the effect of phosphorus and nitrogen heteroatoms on pentahapto coordination of diazaphospholyl ligands in binuclear ruthenium and iron carbonyl derivatives

Theodor Danescu, Alexandru Lupan, Radu Silaghi-Dumitrescu, R. Bruce King

Summary: The structures and energies of complexes containing (Me2C2N2P)2Ru2(CO)n and (Me2C2N2P)2Fe2(CO)n have been studied. Low-energy structures are characterized by the presence of bridging diazaphospholyl rings, while higher-energy structures involve different ligand structures.

JOURNAL OF ORGANOMETALLIC CHEMISTRY (2024)

Article Chemistry, Inorganic & Nuclear

Bis-oxazoline derivatives as ancillary ligands for bis-cyclometalated iridium complexes

Savannah C. Kapper, Aamani Ponnekanti, Jonas Schaab, Tian-yi Li, Christine L. Chung, Gael Ung, Peter I. Djurovich, Mark E. Thompson

Summary: Organometallic iridium complexes with two cyclometalated ligands and one bis-oxazoline derived ancillary ligand were studied. These complexes have emission spanning across the visible and near-ultraviolet region, with moderate to high photoluminescence quantum yields. The (ppy)2Ir(BOX-CN) complexes were resolved into Delta- and Lambda-diastereomers based on solubility differences.

JOURNAL OF ORGANOMETALLIC CHEMISTRY (2024)

Article Chemistry, Inorganic & Nuclear

Sonochemical synthesis of 1,2,4,5-tetrasubstituted imidazoles catalyzed by reusable reactive magnetic cobalt copper ferrite nanoparticles as a synergistic effect

Zahra Karimi Sangari, Hossein Naeimi

Summary: In this research, a nanostructured CoCuFe2O4 catalyst was prepared using a brief and useful synthetic strategy. This catalyst was used for synthesizing 1,2,4,5-tetrasubstituted imidazole derivatives under ultrasonic irradiation. The approach offers advantages such as high efficiency, short reaction times, simplicity of the reaction medium, accelerated reaction rates, and easier separation and purification of products.

JOURNAL OF ORGANOMETALLIC CHEMISTRY (2024)

Article Chemistry, Inorganic & Nuclear

Ferrocene based Schiff bases and their complexes: Synthesis characterization and biological evaluation

Rukhsana Gul, Wajid Munir, Ebraheem Abdu Musad Saleh, Shaukat Shujah, Muhammad Sirajuddin, Saira Tabassum, Khalil Ur Rehman, Dilfaraz Khan, Sameerah I. Al-Saeedi, Ehab A. Abdelrahman

Summary: Two new Schiff base ligands were synthesized and used to form copper, nickel, and cobalt complexes. The synthesized compounds were characterized and screened for various biological activities. The metal complexes showed better activities in antibacterial, antifungal, antidiabetic, and antioxidant assays.

JOURNAL OF ORGANOMETALLIC CHEMISTRY (2024)

Review Chemistry, Inorganic & Nuclear

Recent advances on graphitic carbon nitride-based S-scheme photocatalysts: Synthesis, environmental applications, and challenges

Ahsan Nazir, Pengwei Huo, Ameena Tur Rasool

Summary: This review explores the potential of g-C3N4-based S-scheme heterojunctions in addressing environmental issues. It summarizes the mechanism and preparation techniques of S-scheme heterojunctions based on g-C3N4, and presents recent studies on their applications in pollutant removal, CO2 reduction, hydrogen production, and bacterial disinfection. The review concludes with an outlook on future challenges for g-C3N4-based S-scheme heterojunctions.

JOURNAL OF ORGANOMETALLIC CHEMISTRY (2024)

Article Chemistry, Inorganic & Nuclear

Pd-PEPPSI catalysts bearing N-heterocyclic carbene ligands derived from caffeine and theophylline for Mizoroki-Heck and C(sp2)-H arylation reactions

Francois Mazars, Koffi Senam Etse, Guillermo Zaragoza, Lionel Delaude

Summary: The activity of three Pd-PEPPSI catalyst precursors with N-heterocyclic carbene (NHC) ligands derived from caffeine and theophylline in Mizoroki-Heck reactions was tested. The results showed that the catalysts achieved high conversions and yields, especially in the presence of electron-withdrawing substituents.

JOURNAL OF ORGANOMETALLIC CHEMISTRY (2024)

Article Chemistry, Inorganic & Nuclear

A low cost and energy consumption Ultra-microporous CPM-20(Co) for CO2/N2 and CO2/CH4 separation

Bo-Han Wu, Xue Zhou, Lin Liu, Zheng-Bo Han

Summary: Researching carbon dioxide removal from flue gas and natural gas is crucial. Metal-organic frameworks (MOFs) are commonly used in adsorption due to their high surface area, porosity, and chemical properties. An ultra-microporous MOF CPM-20(Co) with mixed ligand was synthesized using inexpensive ligands. The material exhibited high selectivities and low regenerative energy, making it a promising option for CO2 separation in industries.

JOURNAL OF ORGANOMETALLIC CHEMISTRY (2024)