Mechanistic Insight into the Catalytic Staudinger Ligation

White, Paul B.; Rijpkema, Sjoerd J; Bunschoten, Roderick P; Mecinović, Jasmin

doi:10.1021/acs.orglett.8b04035

Cited by 12 publications

(20 citation statements)

References 29 publications

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“…Mecinović later demonstrated an ambient temperature protocol by employing an optimized hydrosilane reductant . Catalytically formed iminophosphoranes from PPh 3 ( P11 ) can also be used for Staudinger amidation reactions (Figure B), although the precise mechanism of the redox cycle is unclear. − …”

Section: State-of-the-art Developments In Organopnictogen Redox Catal...mentioning

confidence: 99%

Main Group Redox Catalysis of Organopnictogens: Vertical Periodic Trends and Emerging Opportunities in Group 15

2021

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A growing number of organopnictogen redox catalytic methods have emergedespecially within the past 10 yearsthat leverage the plentiful reversible two-electron redox chemistry within Group 15. The goal of this Perspective is to provide readers the context to understand the dramatic developments in organopnictogen catalysis over the past decade with an eye toward future development. An exposition of the fundamental differences in the atomic structure and bonding of the pnictogens, and thus the molecular electronic structure of organopnictogen compounds, is presented to establish the backdrop against which organopnictogen redox reactivityand ultimately catalysisis framed. A deep appreciation of these underlying periodic principles informs an understanding of the differing modes of organopnictogen redox catalysis and evokes the key challenges to the field moving forward. We close by addressing forward-looking directions likely to animate this area in the years to come. What new catalytic manifolds can be developed through creative catalyst and reaction design that take advantage of the intrinsic redox reactivity of the pnictogens to drive new discoveries in catalysis?

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Section: State-of-the-art Developments In Organopnictogen Redox Catal...mentioning

confidence: 99%

Main Group Redox Catalysis of Organopnictogens: Vertical Periodic Trends and Emerging Opportunities in Group 15

2021

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“…Undoubtedly, O’Brien’s 2009 report on a catalytic Wittig reaction, in which a silane reduces the phosphine oxide byproduct back to phosphine in situ during the reaction, unleashed the imaginations of researchers around the world . Consequently, the subsequent decade witnessed numerous accounts of catalytic versions of classical P(V)O-generating reactions, including Wittig olefination, Appel reaction, Staudinger reduction, Staudinger ligation, aza-Wittig reaction, Mitsunobu reaction, and Cadogan cyclization, with all employing stoichiometric silanes as terminal reductants. , While studies of redox-driven phosphine oxide catalysis of the aforementioned reactions have continued, − the past two years have been marked by the application of redox-driven phosphine oxide catalysis to lesser-known reactions.…”

Section: Phosphine Oxide Catalysismentioning

confidence: 99%

Phosphorus-Based Catalysis

et al. 2021

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Phosphorus-based organocatalysis encompasses several subfields that have undergone rapid growth in recent years. This Outlook gives an overview of its various aspects. In particular, we highlight key advances in three topics: nucleophilic phosphine catalysis, organophosphorus catalysis to bypass phosphine oxide waste, and organophosphorus compound-mediated single electron transfer processes. We briefly summarize five additional topics: chiral phosphoric acid catalysis, phosphine oxide Lewis base catalysis, iminophosphorane super base catalysis, phosphonium salt phase transfer catalysis, and frustrated Lewis pair catalysis. Although it is not catalytic in nature, we also discuss novel discoveries that are emerging in phosphorus(V) ligand coupling. We conclude with some ideas about the future of organophosphorus catalysis.

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“…Denton demonstrated that the silane cannot be simply regarded as an innocent terminal reductant in these processes, 29 and subsequently White and Mecinović provided further mechanistic insight. 30…”

Section: Reviewmentioning

confidence: 99%