Amine-Directed Hydroboration: Scope and Limitations

Scheideman, Matthew; Wang, Guoqiang; Vedejs, E.

doi:10.1021/ja0774663

Cited by 62 publications

(32 citation statements)

References 51 publications

(41 reference statements)

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“…Intramolecular versions of the hydroboration process using tethered, unsaturated amine iodoborane complexes work especially well, but these reactions are also believed to take place without dissociation to borenium species. 106 …”

Section: Borenium Reagents For C-b Bond Formationmentioning

confidence: 99%

Cationic Tricoordinate Boron Intermediates: Borenium Chemistry from the Organic Perspective

2012

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CONTENTS 1. Introduction 4246 2. History of Borenium Ions: Often Considered, Seldom Confirmed 4247 2.1. Suspected Intermediates in B−N Protonation 4247 2.2. Hypothetical Isomers of Cl 3 B•NHMe 2 4247 2.3. The First Observable Borenium Salt 4247 2.4. Nucleophilic Substitution of X 3 B•NR 3 and Py•BF 2 X 4248 2.5. Aminoborenium Ions, Stabilization by n-Delocalization 4249 3. Recent Developments in the Generation of Observable Borenium Intermediates 4249 3.1. Electrophilic Activation by Protonation or by Lewis Acid Catalysis 4249 3.2. Halide Abstraction by a Halophile 4250 3.3. The Borinium−Borenium Interface: Gas-Phase Oxyborenium Ions 4251 3.4. Borenium Salt Generation by Hydride Abstraction 4251 3 . 4 . 1 . H y d r i d e A b s t r a c t i o n b y T r i s -(pentafluorophenyl)borane 4251 3.4.2. Hydride Abstracton by Trityl Salts 4252 3.4.3. Hydride-Bridged Borenium Salt Dimers 4252 3.5. Borenium Ion Generation by Nucleophilic Addition−Heterolysis 4253 4. Borenium Lewis Acidity vs Structure 4254 4.1. Experimental Evaluation of Lewis Acidity 4254 4.2. Computational Evaluation of Borenium Lewis Acidity 4255 5. Borenium Ions and Stereogenic Boron 4257 5.1. Racemization by Heterolysis 4257 5.2. Asymmetric Memory at Stereogenic Boron 4257 5.3. Chiral Salicylaldimine Boronate Complexes 4258 6. Enantioselective Catalysis and Chiral Borenium Ions 4259 6.1. The Dual Function of Oxazaborolidines in the CBS Reduction 4260 6.2. The Role of Borenium Species in Diels−Alder Catalysis 4261 6.3. Reactivity and Scope of Oxazaborolidine-Derived Diels−Alder Catalysts 4263 6.4. Miscellaneous Uses of Chiral Borenium Lewis Acid Catalysts 4265 7. Miscellaneous Applications of Borenium Lewis Acids 4266 7.1. B−O Activation 4266 7.2. Lewis Acidity and π-Conjugated Borenium Analogues 4267 7.3. π-Conjugated Borenium Analogues as Selective Anion Sensors 4268 7.4. Tricoordinate Boron in Structures Containing Metal Cations 4269 8. Borenium Reagents for C−B Bond Formation 4269 8.1. Borenium Ion Equivalents 4269 8.2. Do Borenium Ions Participate in Hydroboration Chemistry? 4270 8.3. Borenium Equivalents in Electrophilic Aromatic Borylation 4271 8.3.1. Intramolecular Borylation 4271 8.3.2. Intermolecular Borylation 4272 8.3.3. Recent Developments in Muetterties Borylation (BX3 plus Proton Scavenger) 4275 9. Extension of Borenium Chemistry to Neighboring Fields and Unusual Environments 4276 9.1. N-Heterocyclic Carbenes as Stabilizing Ligands for Borenium Salts 4276 9.2. Miscellaneous Related Topics Involving BH Species 4277 10. Summary 4278 Author Information 4279 Corresponding Author 4279 Notes 4279 Biographies 4279 Acknowledgments 4279 References 4279

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Section: Borenium Reagents For C-b Bond Formationmentioning

confidence: 99%

Cationic Tricoordinate Boron Intermediates: Borenium Chemistry from the Organic Perspective

2012

Self Cite

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“…The intermediacy of borenium cations (or their functional equivalents) in hydroboration was first considered by Vedejs and co-workers when studying the reactivity of (L)BH 2 X (X¼I or OTf, L¼amine or phosphine) [75][76][77]. Importantly, the hydroboration reactivity of the (L)BH 2 X species was distinct to that of the free borane, particularly in providing improved regioselectivity.…”

Section: Hydroborationmentioning

confidence: 99%

Fundamental and Applied Properties of Borocations

Ingleson

2015

Synthesis and Application of Organoboron Compounds

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“…A series of phenethylamines, important substructures in biologically relevant molecules such as dopamine, amphetamine, and adrenaline, have recently been prepared by the hydroboration of enamines using 9-BBN [39]. Although the amine-directed uncatalyzed hydroboration using H 3 BÁTHF is known [40,41], to the best of our knowledge, the metal catalyzed hydroboration of enamines has not yet been reported. While a number of different transition metals are known to catalyze hydroborations, reactions employing rhodium complexes are the most common.…”

Section: Resultsmentioning

confidence: 99%