Page 1333 - Advanced Organic Chemistry Part B - Reactions & Synthesis

1310 Friedel-Crafts alkylation reaction (Cont.) in nucleophilic substitution, 223
intramolecular, 1016–1017 in hydride reduction of halides, 422
Index Lewis acid catalysts for, 1008–1010 HMPA, see Hexamethylphosphoric triamide
rearrangement during, 1014–1015 Hofmann-Loeffler-Freytag reaction, 990
scandium triflate catalysis, 1017 Hofmann rearrangement, 949–950, 955
Fries rearrangement, 1023 Hydration
alkenes by oxymercuration, 294–298
alkenes by strong acid, 293–294
Gabriel amine synthesis, 229–230
alkynes, 335
Gif oxidation, 1150
Hydrazones, chiral
Glycols, see Vic-diols
anions, alkylation of, 52–54
Glycosylation
auxiliaries for alkylation, 532
Mitsunobu reaction in, 231
organocerium addition to, 666
Grignard reagents, see Magnesium,
Hydrazones, N-sulfonyl
organo- compounds
alkenes from, 454
Grob fragmentation, 461, 897, 899
carbenes from, 913
organolithium reagents from, 454–456, 631
Halides reduction of, 453
alkenyl Hydrosilation, 809–814
coupling by nickel compounds, 754 catalysts for, 810–812
cross-coupling, Pd-catalyzed, 723–730 N-hydroxybenzotriazole
from alkynes, 352–3 as co-reagent in amide synthesis, 253
alkyl N-hydroxysuccinimide
from alcohols, 217–223 as co-reagent in amide synthesis, 253–254
reduction by hydride reagents, 422–424 Hydride donor reagents
reduction by hydrogen atom donors, table of, 397
431–434 Hydroalumination, 353–357
aryl Hydroboration
coupling by copper, 703–705 alkenes, 337–344
coupling by nickel compounds, 756 by catechol borane, 340
cross-coupling, pd-catalyzed, 723–730 enantioselective, 347–351
from diazonium ions, 1030–1032 by halo boranes, 340
from aromatic halogenation, 1008–1014 metal-catalyzed, 341–344
reactions with by pinacol borane, 340
lithium, 624 regioselectivity of, 337–338
magnesium, 621–622 stereochemistry of, 344
organocopper compounds, 675, thermal reversibility, 342–344
695–697 alkynes, 353
reductive dehalogenation, 431–432, 439 Hydroformylation, 759–760
examples, 431, 442 Hydrogen atom donors
Halogenation in reductions, 431–434
acyl chlorides, 331 tri-n-butylstannane as, 431–433
alkenes, 298–301 Hydrogenation, 368–387
reagents for, 305 of functional groups, table, 390
alkynes, 333–336 heterogeneous catalysis of, 369–374
aromatic, 1008–1014 alkynes, partial, 387
ketones, 328–330 mechanism of, 369–370
reagents for, 305 substituent directive effects in, 373
Heck reaction, 715–723 stereoselectivity of, 370–372
examples, 721–722 homogeneous catalysis of, 374–376
intramolecular -amido acrylic acids, 380, 384
in Baccatin III synthesis, 1215 computational model for, 380–382
mechanism, 716–717 Crabtree catalyst in, 375–377
regiochemistry of, 719–720 enantioselective, 376–387
substituent effects in, 719–720 examples, 376, 384–385
Hexamethylphosphoric triamide (HMPA) styrene derivatives, 386–387
as solvent, 18 Wilkinson’s catalyst in, 374
enolate reactivity, effect on 20 ketones
enolate stereochemistry, effect on, 568 enantioselective, 391–395