Nov 9, 2017 - Published 2018 by John Wiley & Sons, Inc. ArH + RCH CHX. ArCHRCH,X chiral. X= CHO, COR, COR. 343. ç®æ
Comprehensive Organic Transformations
ラロック有機変換ガイド
A Guide to Functional Group Preparations, 3rd Edition
Edited by Richard C. Larock, Iowa State University, Ames
世界中の有機合成化学者に愛用さ れてきたRichard C. Larock（アイ オワ州立大名誉教授）による記念碑的 著作を、約20年ぶりに待望の改訂
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– Angewandte Chemie review of the 2nd edition
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Page 344
344
Alkanes and Arenes
3. FRIEDEL-CRAFTS AND RELATED ALKYLATION REACTIONS
+ ArCR2
R1
CH2
catalyst
Ar CR2CH3
R1
R1 = Me, OMe, OH R2 = H, Me, Ph Catalyst
Richard C. Larock and Alexandre A. Pletnev
For the metal-catalyzed cross-coupling of alkyl halides and arenes, see page 295, Section 2.24 (Fe); page 296, Section 2.25 (Ru); page 299, Section 2.26 (Co); page 302, Section 2.29 (Ni); page 304, Section 2.30 (Pd); and page 336, Section 2.37 (miscellaneous reagents). For coupling reactions mainly directed to the synthesis of biaryls, see page 194, Section 1. For the reaction between arenes and carbonyl compounds leading to benzylic alcohols, see page 2405, Section 2.2. For the reaction between arenes and imines leading to benzylic amines, see page 1650, Section 3.
Ca(NTf2)2, (n-Bu4N)PF6
Chem Eur J 16 11264 (2010)
InCl3-SiO2
SL 1096 (2008)
BiCl3
Eur JOC 4231 (2006)
Sc(OTf)3), ionic liquids
SL 3050 (2007)
Mo(CO)6
CL 851 (1997)
X + R2CH
R1
CHY
catalyst
X R1
R1 = H, Me, OR, fused arene
CHR2CH2Y
Reviews:
General reviews: Org Rxs 3 1 (1946) Quart Rev 8 355 (1954) Ind Eng Chem 47 1926 (1955); 48 1670 (1956) “Friedel-Crafts and Related Reactions,” Ed. G. A. Olah, Interscience, New York (1964), Vol 2 G. A. Olah, “Friedel-Crafts Chemistry,” Wiley-Interscience, New York (1973) R. M. Roberts, A. A. Khalaf, “Friedel-Crafts Alkylation Chemistry,” M. Dekker, New York (1984) “Comprehensive Organic Synthesis,” Eds. B. M. Trost and I. Fleming, Pergamon, Oxford (1991), Vol 3, Part 1.8, p 293 J. A. Campbell, “Asymmetric Friedel-Crafts Reaction: Past to Present” in “Name Reactions for Carbocyclic Ring Formations,” Ed. J. J. Li, John Wiley & Sons, Inc., Hoboken, NJ (2010), p 600 Int J Pharm Chem Biol Sci 2 52 (2012)
ArH
+
C
C
Ar
C
C
H
Angew Int 38 1698 (1999) Chem Rev 110 624 (2010) X
R2
Y
Catalyst
NR2
Ph
H
SL 243 (1999)
OH
alkyl Ar
H NO2
[Rh(COD)2]BF4, PPh3, HBF4OEt2
Re2(CO)10 organocatalyst (enantioselective)
JACS 131 9914 (2009) CC 2228 (2007) Angew Int 49 7299 (2010)
COR
H
alkyl, Ar, SiR3
RuH2(CO)(PPh3)3
Si(OR)3
RuH2(CO)(PPh3)3
Nature 366 529 (1993) Pure Appl Chem 69 589 (1997) Acct Chem Res 35 826 (2002) JACS 132 17741 (2010) BCSJ 70 3117 (1997)
CO2R, CN
H
Si(OR)3
RuH2(CO)(PPh3)3
Acct Chem Res 35 826 (2002) Adv Syn Catal 345 1077 (2003)
For additional metal-catalyzed couplings between arenes and olefins, see page 296, Section 2.25 (Ru); page 299, Section 2.26 (Co); page 299, Section 2.27 (Rh); and page 301, Section 2.28 (Ir).
See the general reviews of the Friedel-Crafts reaction listed above.
ArH + RCH
Comprehensive Organic Transformations: A Guide to Functional Group Preparations, Third Edition. By Richard C. Larock. © 2018 Richard C. Larock. Published 2018 by John Wiley & Sons, Inc.
CHX
ArCHRCH2X chiral
X = CHO, COR, CO2R
343
目次の一部 • • • • •
Reduction Coupling Reactions Friedel-Crafts And Related Alkylation Reactions Ring-Forming Reactions Aromatization
Alkenes • Isomerization Of Alkenes • Elimination • Alkylidenation Of Carbonyl And Related Compounds • Wittig And Related Reactions • Metal-Promoted Coupling Reactions • Arene, Alkyne, And Diene Addition Reactions • Dienes And Polyenes • Diels–Alder Reactions • Cyclization, Annulation, And Related Reactions • Isomerization And Metathesis • Elimination Reactions • Wittig And Related Approaches • Alkylation, Alkenylation, And Arylation Of Alkynes And Allenes
Halides • • • • • • • • • • •
Halogenation Of Hydrocarbons Aromatic Halogenation Halogenation Of Alkenes And Dienes Halogenation Of Alkynes Interconversion Of Halides Halogenation Of Nitrogen Compounds Halogenation Of Ethers Halogenation Of Alcohols Halogenation Of Phenols Halogenation Of Sulfur And Selenium Compounds Halogenation Of Carbonyl And Related Compounds
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• Halodecarboxylation And Decarbonylation Of Acids And Derivatives • Halogenation Of Organometallics
Amines • • • • • • • • • • • • •
From Alkanes From Arenes From Alkenes, Dienes, And Alkynes From Alkyl And Aryl Halides Or Sulfonates From Other Amines And Derivatives From Azides From Nitro Compounds Heteroatom And Metal Substitution From Ethers, Alcohols, And Derivatives From Aldehydes, Ketones, And Derivatives From Carboxylic Acids And Derivatives From Nitriles From Isonitriles And Azo Compounds
Ethers • From Other Ethers • Alkylation Of Alcohols, Phenols, And Derivatives • Alkane, Arene, Alkene, And Alkyne Substitutions And Additions • Acetal, Carbonyl, And Ortho Ester Conversions • Miscellaneous Reactions
Alcohols And Phenols • • • • • • • • • •
Resolution Alcohol Transposition Substitution Oxidation Alkene, Diene, And Alkyne Additions Organoboranes Ether Cleavage Reduction Alkylation Of Carbonyl Compounds Miscellaneous Reactions
Aldehydes And Ketones • Carbonyl Transposition • Oxidation • Reduction Of Phenols, Carboxylic Acids And Derivatives, And Nitriles • Rearrangements • Condensation Reactions • Cyclization And Annulation Reactions • Carbonylation And Related Reactions • Electrophilic Acylation • Nucleophilic Acylation • Sulfur, Selenium, And Tellurium Reagents • Heterocycles • Carbonyl Homologation • Alkylation And Acylation Of Aldehydes, Ketones, And Their Derivatives • Alkylation Of Α- And Β-Substituted Carbonyl Compounds • 1,4-Addition To Α,Β-Unsaturated Carbonyl Compounds And Derivatives
Nitriles, Carboxylic Acids, And Derivatives • Oxidation, Substitution, And Addition • Reduction • Carbonylation, Carboxylation, And Related Reactions • Carbonyl Homologation And Degradation • Alkylation, Acylation, And Substitution Of Nitriles, Carboxylic Acids, And Derivatives • Conjugate Addition To Α,Β-Unsaturated Nitriles, Carboxylic Acids, And Derivatives • Rearrangements • Lactone And Lactam Formation • Interconversion Of Nitriles, Carboxylic Acids, And Derivatives • Miscellaneous Reactions
17-321711
Alkanes And Arenes
