UID:
almahu_9949984037502882
Umfang:
1 online resource (394 pages)
ISBN:
9780323859240
Inhalt:
Comprehensive Aryne Synthetic Chemistry summarizes the progress in the synthetic utilization of arynes for noncatalytic and transition metal-catalyzed reactions developed in the last 20 years. The book covers a broad range of topics including methods of generating arynes, regioselectivity, electrophilic couplings, pericyclic reactions, transition metal-catalyzed reactions, and cycloadditions.
Anmerkung:
Intro -- Comprehensive Aryne Synthetic Chemistry -- Copyright -- Contents -- Contributors -- Chapter 1: General introduction to comprehensive aryne synthetic chemistry -- 1. Introduction -- 2. Prologue: Before the concept of arynes -- 3. Dawn of aryne synthetic chemistry -- 4. The Kobayashi method -- 5. Past, present, and future -- References -- Chapter 2: Electrophilic Couplings -- Chapter 2.1: Simple arylation -- 1. Introduction -- 1.1. N-Arylation -- 1.2. O-Arylation -- 1.3. C-Arylation -- 1.3.1. C-Arylation of carbonyl α-position -- 1.3.2. C-Arylation of sp2 carbon -- 1.3.3. C-Arylation of sp carbon -- 1.3.4. C-Arylation of sp3 carbon -- 1.4. S-Arylation -- 1.5. P-Arylation -- 1.6. F-Arylation -- 1.7. B-Arylation -- 1.8. Sn-Arylation -- 1.9. Regioselectivity of simple arylation -- References -- Chapter 2.2: Insertion into σ-bonds -- 1. Introduction -- 2. Four categories of aryne insertion reactions depending on reaction pathways -- 3. Aryne insertion reactions initiated by nucleophilic attack of N atom -- 4. Aryne insertion reactions initiated by nucleophilic attack of C atom -- 4.1. Aryne insertion-one-pot reaction -- 4.2. Aryne insertion-tandem reaction -- 4.3. Other types of reaction -- 5. Aryne insertion reactions initiated by nucleophilic attack of other atoms -- 6. Regioselectivity -- 6.1. 3-Methoxybenzyne -- 6.2. 3-Haloarynes -- 6.3. 3-Methylbenzyne -- 6.4. 3-Silyl(or boryl)arynes -- 6.5. 3,5-Dimethoxybenzyne -- 6.6. 1,2-Naphthalyne -- 6.7. Small-ring-fused arynes -- 6.8. 4-Substituted arynes -- 6.9. Hetarynes -- 7. 1,2-Benzdiyne chemistry in aryne insertion reactions into σ-bonds -- 7.1. Normal insertion reactions of 3-triflyloxybenzyne into a σ-bond -- 7.2. Aryne relay method -- 7.3. Domino aryne process -- 8. Aryne insertion reactions into σ-bonds vs simple arylation -- 8.1. Effect of reaction media concentration.
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8.2. Effect of solvents -- 9. Efficiency of insertion reactions with various arynes -- 10. Aryne route to natural products and bioactive molecules -- References -- Chapter 2.3: Multicomponent reactions -- 1. Nucleophilic addition-induced MCRs -- 1.1. Carbon-centered nucleophiles -- 1.1.1. Isocyanides -- 1.1.2. Active methylenes and methines -- 1.1.3. Trifluoromethylation of arynes -- 1.2. Nitrogen-centered nucleophiles -- 1.2.1. Amine nucleophiles -- 1.2.2. Ring opening of cyclic amines -- 1.2.3. Imines and azaarenes -- 1.3. Oxygen-centered nucleophiles -- 1.4. Sulfur-centered nucleophiles -- 1.5. Phosphorus-centered nucleophiles -- 1.6. Halogen-centered nucleophiles -- 2. π-Bond insertion-induced aryne MCRs -- 2.1. CX-bond insertion -- 2.2. SO-bond insertion -- 2.3. NX-bonds and PX-bond insertion -- 3. Cycloaddition-induced aryne MCRs -- 4. Summary -- References -- Chapter 2.4: Molecular rearrangements -- 1. Introduction -- 2. Early reports on rearrangements involving aryne intermediates -- 3. Molecular rearrangements via arynes generated by Kobayashi method -- 3.1. Rearrangement of N-oxides with arynes -- 3.2. Reaction of N-substituted imidazoles with arynes -- 3.3. Synthesis of acridones and acridines -- 3.4. Aryne insertion into thiourea -- 3.5. Aryne-promoted Curtius-type rearrangement -- 3.6. Reaction of arynes with nitrosoarenes -- 3.7. Aza-Claisen rearrangement -- 3.8. Thia-fries rearrangement -- 3.9. N-Heterocycle-triggered rearrangements -- 3.10. Rearrangements triggered by isocyanides -- 3.11. Sulfilimine-triggered rearrangements -- 3.12. C3-Arylation of indoles -- 3.13. Oxythiolation of arynes -- 3.14. Benzylic-type rearrangement -- 3.15. Smiles rearrangement involving arynes -- 3.16. Vinyl sulfoxide-triggered rearrangements -- 3.17. Aryne-1,2,3-trifunctionalization with aryl allyl sulfoxides.
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3.18. Hydroxycoumarin-triggered rearrangement -- 3.19. Ketoximes-triggered rearrangements via arynes -- 3.20. Brook rearrangement -- 3.21. Stevens rearrangement -- 3.22. Oxa-[2,3] sigmatropic rearrangement via arynes -- 4. Molecular rearrangements involving HDDA arynes -- 5. Conclusion -- References -- Chapter 3: Pericyclic reactions including [2+2], [3+2], and [4+2] cycloadditions -- 1. Introduction -- 2. [4+2] cycloaddition -- 2.1. Cyclic dienes -- 2.1.1. Furans and related species -- 2.1.2. Pyrrole and related species -- 2.1.3. Pyranones -- 2.1.4. Anthracenes -- 2.1.5. Other cyclic dienes -- 2.2. Acyclic carbo-1,3-dienes -- 2.3. Hetero-1,3-dienes -- 2.4. Intramolecular Diels-Alder reaction -- 2.5. Asymmetric Diels-Alder reactions -- 3. [2+2] cycloaddition -- 3.1. Substituted benzocyclobutenes -- 3.2. Highly oxidized benzocyclobutene derivatives -- 3.3. [2+2] cycloaddition with carbon-heteroatom double bonds and heteroatom double bonds -- 4. [3+2] cycloaddition -- 4.1. Nitrones -- 4.2. Nitrile oxides -- 4.3. Nitrile imine -- 4.4. Diazo compounds -- 4.5. Azides -- 4.6. Oxidopyridinium and pyridine N-oxide -- 4.7. Cyclic 1,3-dipoles -- 5. Reaction integrations using aryne pericyclic reaction -- 5.1. The reaction integration using polyaryne species -- 5.2. The reaction integration using donor-acceptor molecules -- 5.3. Cascade reaction -- 6. Conclusion -- References -- Chapter 4: Transition-metal-catalyzed reactions -- 1. Introduction -- 2. Metal complexes of benzyne -- 2.1. Synthesis of transition-metal complexes of benzyne -- 2.2. Reactions of transition-metal complexes of benzyne -- 2.2.1. Early transition-metal complexes of benzyne -- 2.2.2. Late transition-metal complexes of benzyne -- 3. Pd-catalyzed aryne reactions -- 3.1. [2+2+2] Reactions -- 3.1.1. Cyclotrimerization reactions of arynes -- 3.1.2. Cocycloaddition of arynes and alkynes.
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3.1.3. Cocycloaddition of arynes and diynes -- 3.1.4. Cocycloaddition of arynes and allenes -- 3.2. Multicomponent coupling reactions -- 3.2.1. Reaction of arynes involving alkyl halides and organostannane -- 3.2.2. Reaction of arynes involving alkyl halides and alkynes -- 3.2.3. Reaction of arynes involving aryl halides and alkenes -- 3.2.4. Reaction of arynes involving aryl halides and alkynes -- 3.3. Cascade cyclizations -- 3.4. σ-Bond insertion reactions -- 3.4.1. Insertions into carbon-heteroatom bonds -- 3.4.2. Insertions into heteroatom-heteroatom bonds -- 4. Cu-catalyzed aryne reactions -- 4.1. Insertion of aryne into CCu bond -- 4.1.1. Insertion into CspCu bond -- 4.1.2. Insertion into Csp2Cu bond -- 4.1.3. Insertion into Csp3Cu bond -- 4.2. Insertion of aryne into the BCu bond -- 4.3. Insertion of aryne into PCu bond -- 4.4. Insertion of aryne into CuCF3 bond -- 5. Ag-catalyzed aryne reactions -- 5.1. The effect of silver in aryne reactions -- 5.2. Intramolecular C-H insertion reactions -- 5.3. Intra- and intermolecular hydroarylation reactions -- 6. Ni-catalyzed aryne reactions -- 6.1. Cycloaddition reactions of arynes -- 6.1.1. [2+2+2] Cycloaddition reactions -- 6.1.2. [4+2] Cycloaddition reactions -- 6.2. Other cyclization reactions -- 7. Other transition-metal-catalyzed aryne reactions -- 7.1. Pt-catalyzed aryne reactions -- 7.2. Au-catalyzed aryne reactions -- 8. Conclusions -- References -- Index.
Weitere Ausg.:
Print version: Yoshida, Hiroto Comprehensive Aryne Synthetic Chemistry San Diego : Elsevier,c2022 ISBN 9780323851534
Sprache:
Englisch
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