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343 3-Acetamido-5-Acetylfuran (3A5AF)

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343 3-Acetamido-5-Acetylfuran (3A5AF) 445 Index a α-alkyl acrylates 175, 176 AADH 252 α-aminobutyric acid 366 AADH vs. AmDH 254 α-aminophosphonates 357 2-acetamide-2-deoxyisosorbide (ADI) α-aminophosphonic acids 357 343 α,β-unsaturated 2-acylimidazoles 3-acetamido-5-acetylfuran (3A5AF) 177 343 AmDH (amine dehydrogenase) 128, 2-acetamido-2-deoxysorbitol (ADS) 129, 252–262 342 amine dehydrogenase (AmDH) 128, acrylamine 344 129, 252–262 active pharmaceutical ingredients cascade reactions (APIs) 12, 25, 158, 161, 188, biocatalytic hydrogen borrowing 246, 399, 431–435 261 alanine 127, 257, 262, 361, 364–366 chemoenzymatic cascades 262 alanine dehydrogenase (AlaDH) 127 multi-enzyme cascades 261–262 alcohol dehydrogenases (ADH) 128, leucine dehydrogenase 253–254 129, 261 native amine dehydrogenase alfuzosin 367 254–256 aliphatic amines 67, 74, 131, 133, 244, phenylalanine dehydrogenase 254 289, 312, 355, 357 substrate promiscuity aliphatic N-nitrosamines 432 amino alcohol synthesis 260 alkanolamines 348–350 reductive aminase activity alkene-alkyne (enyne) metathesis 139 259–260 alkyl amines 306, 307 synthetic applications capping agents 322–325 primary amine synthesis 256–258 displacement, of amines 325 amidyl radical addition 55–62 alkyl aryl ketones 160 amination via N-atom nucleophilic alkylazo compounds 432 addition α,α-disubstituted benzylamine aromatic C(sp2)-H bonds amination picolinamides 396 77–82 Methodologies in Amine Synthesis: Challenges and Applications, First Edition. Edited by Alfredo Ricci and Luca Bernardi. © 2021 WILEY-VCH GmbH. Published 2021 by WILEY-VCH GmbH. 446 Index amination via N-atom nucleophilic 3-amino-1,2,4-triazole 358 addition (contd.) 2-and 4-nitrocumene 428 benzylic C(sp3)-H bonds amination aniline 382 85–87 synthesis 403 N-α-C(sp3)-H bonds amination annulated aniline derivative 382 87–90 anti-cancer alkaloid proximicin A olefinic C(sp2)-H bonds amination 344 82–85 anti-cancer drugs 367 amination via radicals cross-coupling antihypertensives 352 aryl C(sp2)-N bonds formation via antiseptic agents 352 radicals cross-coupling 94–96 arene amination 392, 393, 397, 398, C–N bonds formation 96–98 400 arene nucleophiles 390 using diarylamines 91 arginine and ethylenediamine (NCDs) amine-functionalized graphene (AFG) 312 299 CD-supported amines 315 amine oxidases (AOs) 103, 155, 214, one-pot functionalization 312, 313 243–252, 266, 274 post-functionalization 313–315 amines aromatic amination reactions and formamides synthesis 345–348 human pharma application aminium radical cation addition 432–433 64–71 recycling of metals, ligands and other amino α-carbanion 204 cost drivers of 434 aminoalkylphenol derivatives 367, regulated part of new drug 368 applications 434–435 amino-functionalization, of CNO transition metal accounting 433 308–309 aromatic amines 68, 249, 354, 361, amino functionalized carbon-based 362, 377, 378, 415, 429, 431 nanomaterials 308–309 aromatic C(sp2)-H bonds amination 3-aminofuran 344 77 aminoketones 362, 364, 365 aromatic C–N bond formation 2-aminophenyl oxazoline 389 approaches 389 2-aminophenyl pyrazole 389 aromatic N,N-dimethyl tertiary amines amino pyrazole 387, 427 367 2-aminopyridine-1-oxide 389, 395 aromatization reactions 310 2-aminopyrimidine hydrochloride Arthrobacter nicotinovorans 252 426 artificial imine reductase (ATHase) 2-aminoquinazolin-4(3H)-one 418 247 8-aminoquinoline 389, 393, 395, 396 artificial transfer hydrogenases benzamide 393, 395 (ATHase) 267 8-aminoquinolinyl 404 arylamine formation 2-aminosugar 344 Chan-Lam coupling 428–429 Index 447 flow amination methods 431 asymmetric hydroaminoalkylation immobilization of 168–170 catalysts/supported catalysts asymmetric hydroaminomethylation 429–431 171–176 nucleophilic aromatic substitution asymmetric hydrogenation (AH) 156, 426–428 171, 172, 434 Pd-catalyzed C–N bond forming asymmetric reductive amination reaction 425–426 156–161, 267, 268, 274, 419 telescoped sequence of nitration and atomic force microscopy (AFM) 312 hydrogenation 428 attenuated total reflectance infrared arylamines 423, 426 (ATR-IR) 297 catalytic C–H amination 389–399 Au(I)/chiral Brønsted acid dual decarboxylative arylamination catalysis 421 405–407 aza-Michael reaction 194, 196 electrochemical approach 402–405 azomethine ylides 291, 292, 295, 305, hydroamination 419–424 307, 346 metal catalyzed cross couplings intermediate 291, 346 414–417 nickel catalyzed C–N coupling b 407–414 Bacillus badius 254, 256, 257 photoredox catalysis 399–402 Bacillus sphaericus 256 reductive amination 417–419 Bacillus steareothermophilus 253 syntheses 389 benchtop stable aminating reagent arylboronates 6, 7, 416 398 aryl bromide 167, 381, 384, 385, 409 benchtop stable ammonium carbamate aryl C–H amination 74, 390, 392–396, 400 398, 417 benzazepines 367–369 aryl C(sp2)-N bonds formation via benzomorpholine 350 radicals cross-coupling benzothiazine 350 other C–N bonds formation 96–98 O-benzoyl hydroxylamines 390 using diarylamines 91 benzylamine 87, 157, 246, 249, 252, aryl-diazonium salts 291, 304, 305 254, 295, 357 aryl fluorosulfonates 413, 414 benzylic amines 259, 318 aryl/heteraoaryl chlorides 412 benzylic C(sp3)-H bonds amination O-aryl hydroxylamines 401 85–87 aspartic acid 310, 311, 366 β-amidoester 344 Aspergillus Niger 214, 244, 245, 247, β-amino alcohols 350 255, 257 β-D-glucopyranosylamine 352 Aspergillus oryzae (AspRedAm) 128, β-1,4-glycosidic bonds 341 129, 268, 419 β-N-glycosidic bond 196 asymmetric hydroamination 162 B(C6F5)3-H2O catalyzed reductive alkene 162 amination 418 448 Index biaryl based ligand BrettPhos 387 c biaryl monophosphine ligands 386 cadmium-catalyzed amination of bicyclic α-amino acid 214 iodobenzene 415 Biginelli reaction 357, 358 camptothecin (CPT) 307 Bingel–Hirsch reaction 299 Candida antarctica lipase B (CAL-B) bio-based 3,4-dialkoxyanilines 367 126 biocatalytic cascade synthesis 266 carbon-based nanomaterials 287 biocatalytic hydrogen borrowing 261, carbon, allotropes of 290 270 carbon nanostructures biodiesel production 361, 364 Au-NR 297 biorenewable aromatic monomers azomethine ylides, cycloaddition 366 291 bis(hydroxylmethylfurfuryl)amines chiral fullerene derivatives 291 (BHMFA) 355 glycidyltrimethylammonium 3,5-bis(trifluoromethyl)benzyl catalyst chloride 293 225 nanotechnological applications 2,5-bis(aminomethyl)furan (BAMF) 291 356 POM cluster 293 2,5-bis(hydroxymethyl)furan (BHMF) radical arylation reaction 291 356 functionalization procedures N,N′-bis(2-hydroxyethyl)-N,N′- 297–299 dimethyl-ethylenediamine carbon-based nanostructures 290, (BHEDMEDA) 349, 350 295, 297 1,3-bis(diphenylphosphanyl)propane carbon dots (CDs) 309 416 amines, as constituent 310–312 3,5-bistrifluoromethyl-benzaldehyde carbon nanocones 301 288 carbon nanodiamonds (CNDs) boron-doped diamond anodes (BDD) 305–307 404 carbon nanoHorns (CNHs) 301–305 2-bromonapthalene 411 carbon nanomaterials bromotrichloromethane (BrCCl3)87 CND 305–307 Brønsted acid (BH) 90, 134, 135, 160, CNH 301–305 161, 165, 418, 421 CNO 307–308 Buchwald–Hartwig amination 378 carbon nano-onions (CNOs) 287, applications 386–388 307–308 catalyst design 385–386 carbon nanotubes (CNTs) 287, 290, limitations 384 291 mechanistic studies 384–385 1,1′-carbonyldiimidazole 190 Buchwald–Hartwig reactions 16, 430 carboxylic ND (ND-ori)-based Buchwald’s flow synthesis 426 supraparticles (ND-SPs) 307 bulky N-heterocyclic carbene (NHC) catalytic C–H amination 389–405 precatalyst 426 CD-promoted organocatalysis 315 Index 449 cellulosic biomass derivatives aryl C(sp2)-N bonds formation via 348–366 radicals cross-coupling 90–96 Chan–Lam coupling 378, 380–383, radical addition to C-C double/triple 428–429 bonds chemical vapor deposition (CVD) 301 amidyl radical addition 55–62 chemoenzymatic cascades 249, 262 aminium radical cation addition chimeric amine dehydrogenase 254 64–71 chiral amine frameworks 155 radical species addition to aromatic chiral amine (R)-α-methylbenzylamine rings 71–76 357 via N-radical species addition chiral amine synthesis, biocatalytic 54–76 strategies 244 cobalt-catalyzed C–H amination 395 chiral amino alcohol 387, 388 colorimetric test 289 chiral bisphosphine-thiourea ligand confocal fluorescence microscopy 158 297 chiral Brønsted acid 134, 160, 421, continuous Pd-catalyzed C–N coupling 422 process 426 chiral metal center 176–177 copper-catalysed heterocyclisation chiral N-arylamine 422 191 chiral pyrrolidinofullerenes 291 copper-catalyzed anti-Markovnikov chiral switch 155 hydroamination 423 chitin 341–345 copper-catalyzed asymmetric chitin-derived N-compound 343 hydroamination 422 chloropyrazine 427 C–H methyl bond 168 copper-catalyzed C–N coupling choline chloride-urea DES 345 reaction C–H pyridination-aminolysis sequence anticipated mechanism of 379 401 different conditions 380 ciprofloxacin 427 copper-catalyzed hydroamination cis-N-(2-methylcyclohexyl) 161 421, 423 ClMe2Si-IPr-Pd complex 430 copper-catalyzed primary aniline Clostridium sticklandii 258 synthesis 397 C–N bond formation copper-doped porous metal oxides amination via N-atom nucleophilic (Cu20-PMO) 367 addition copper(I) hydride catalysis 421 activated C(sp3)-H bonds copper-mediated decarboxylative amination 85–90 amination 406 aromatic C(sp2)-H bonds copper triflate 108, 291 amination 77–82 covalent functionalization 294, 295, olefinic C(sp2)-H bonds amination 303, 307, 314 82–85 cross-dehydrogenative coupling (CDC) amination via radicals cross-coupling 53 450 Index Cu-catalyzed amination reagents 3 deep eutectic solvents (DES) 345, aminoboration of styrenes 9 369, 370 aryl boronates 7 dehydrogenative C–N couplings 91, aryl silanes
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