Bi(I)-Catalyzed Transfer-Hydrogenation with Ammonia-Borane

Journal of the American Chemical Society
Feng WangJosep Cornella

Abstract

A catalytic transfer-hydrogenation utilizing a well-defined Bi(I) complex as catalyst and ammonia-borane as transfer agent has been developed. This transformation represents a unique example of low-valent pnictogen catalysis cycling between oxidation states I and III, and proved useful for the hydrogenation of azoarenes and the partial reduction of nitroarenes. Interestingly, the bismuthinidene catalyst performs well in the presence of low-valent transition-metal sensitive functional groups and presents orthogonal reactivity compared to analogous phosphorus-based catalysis. Mechanistic investigations suggest the intermediacy of an elusive bismuthine species, which is proposed to be responsible for the hydrogenation and the formation of hydrogen.

References

Apr 25, 2003·Nature·Pierre de MarcillacJean-Pierre Moalic
Jun 20, 2007·Dalton Transactions : an International Journal of Inorganic Chemistry·Frances H StephensR Tom Baker
May 14, 2009·Angewandte Chemie·Bijan NekoueishahrakiDietmar Stalke
Feb 25, 2010·Nature·Philip P Power
Aug 3, 2010·Chemical Reviews·Anne StaubitzIan Manners
Oct 29, 2010·Accounts of Chemical Research·Shū Kobayashi, Yasuhiro Yamashita
Dec 3, 2010·Nature Chemistry·Ram Mohan
Jul 4, 2012·Journal of the American Chemical Society·Nicole L DunnAlexander T Radosevich
Jul 19, 2014·Journal of the American Chemical Society·Papri BhattacharyaHairong Guan
Nov 18, 2014·Journal of the American Chemical Society·Wei ZhaoAlexander T Radosevich
Dec 24, 2014·Accounts of Chemical Research·Douglas W Stephan
Jan 8, 2015·Journal of the American Chemical Society·Wei ZhaoAlexander T Radosevich
Apr 16, 2015·Journal of the American Chemical Society·Kyle D ReichlAlexander T Radosevich
May 15, 2015·Angewandte Chemie·Douglas W Stephan, Gerhard Erker
Jan 23, 2016·Chemical Society Reviews·Michael S HillCatherine Weetman
Jun 11, 2016·Chemical Reviews·Natalia V BelkovaElena S Shubina
Nov 20, 2016·Chemistry : a European Journal·Sven SolyntjesBerthold Hoge
Apr 12, 2017·Journal of the American Chemical Society·Yi-Chun LinAlexander T Radosevich
May 11, 2017·Journal of the American Chemical Society·Trevor V NykazaAlexander T Radosevich
May 20, 2017·Chemical Reviews·Joshua E ZweigTimothy R Newhouse
Feb 2, 2018·Angewandte Chemie·Benedikt RitschelCrispin Lichtenberg
Feb 2, 2018·Journal of the American Chemical Society·Trevor V NykazaAlexander T Radosevich
Mar 21, 2018·Chemical Reviews·Terry Chu, Georgii I Nikonov
Apr 24, 2018·Physical Chemistry Chemical Physics : PCCP·David J IngramAndrea Sella
Oct 30, 2018·Journal of the American Chemical Society·Trevor V NykazaAlexander T Radosevich

❮ Previous
Next ❯

Citations

Apr 5, 2019·Angewandte Chemie·Marcus B KindervaterSaurabh S Chitnis
Jul 30, 2019·Chemistry : a European Journal·Monika KořenkováLibor Dostál
Oct 2, 2019·Chemistry : a European Journal·Saurabh S ChitnisDavid N Langelaan
Jun 6, 2020·Chemistry : a European Journal·Ramkumar KannanAjay Venugopal
Mar 28, 2020·Dalton Transactions : an International Journal of Inorganic Chemistry·Vasudeva Rao BakuruSuresh Babu Kalidindi
Sep 26, 2020·Organic & Biomolecular Chemistry·Chiara FaverioMaurizio Benaglia
Jan 18, 2020·Science·Oriol PlanasJosep Cornella
Sep 3, 2020·Chemical Science·Deb Pratim MukhopadhyayCrispin Lichtenberg
Sep 29, 2020·Chemical Communications : Chem Comm·Jiliang ZhouDouglas W Stephan
May 30, 2020·Dalton Transactions : an International Journal of Inorganic Chemistry·Marcus B KindervaterSaurabh S Chitnis
Jun 11, 2020·Chemistry : a European Journal·Coralie GelisFrank Glorius
Dec 17, 2020·Chemistry : a European Journal·Anna HanftCrispin Lichtenberg
Jan 20, 2021·Journal of the American Chemical Society·Jeffrey M LipshultzAlexander T Radosevich
Mar 11, 2021·The Journal of Organic Chemistry·Menghui SongXi-Cun Wang
Apr 17, 2021·Chemical Communications : Chem Comm·Crispin Lichtenberg
Jun 3, 2021·Organic & Biomolecular Chemistry·Manoj K SahooEkambaram Balaraman
Jun 8, 2021·Dalton Transactions : an International Journal of Inorganic Chemistry·Shigeru ShimadaMing Bao
Jun 17, 2020·Journal of the American Chemical Society·Oriol PlanasJosep Cornella
Nov 5, 2020·Journal of the American Chemical Society·Yue PangJosep Cornella
Apr 25, 2020·Inorganic Chemistry·Álvaro García-RomeroRaúl García-Rodríguez
Jan 13, 2021·Journal of the American Chemical Society·Mujahuddin M SiddiquiHerbert W Roesky
Aug 28, 2021·Chemical Reviews·Matthew M D RoyEric Rivard
Nov 2, 2021·Journal of the American Chemical Society·Hayato FujimotoMamoru Tobisu
Dec 17, 2021·Journal of the American Chemical Society·Marc Magre, Josep Cornella
Jan 13, 2022·Dalton Transactions : an International Journal of Inorganic Chemistry·Tomáš ChlupatýAleš Růžička

❮ Previous
Next ❯

Methods Mentioned

BETA
NMR

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.