Reagents for Silicon-Mediated Organic Synthesis

by
Edition: 1st
Format: Hardcover
Pub. Date: 2011-11-07
Publisher(s): Wiley
List Price: $177.42

Buy New

Usually Ships in 3-4 Business Days
$168.97

Rent Textbook

Select for Price
There was a problem. Please try again later.

Digital

Rent Digital Options
Online:1825 Days access
Downloadable:Lifetime Access
$146.40
*To support the delivery of the digital material to you, a non-refundable digital delivery fee of $3.99 will be charged on each digital item.
$146.40*

Used Textbook

We're Sorry
Sold Out

Summary

Over the last three decades the importance of organosilicon chemistry has greatly increased because it has opened a number of new synthetic strategies. Silicon reagents are usually low-cost, versatile and allow a wide range of reactions. This is the first Handbook to compile essential Silicon containing reagents and makes use of the leading reagent database e-EROS. Another hot volume in the series ' Handbooks of Reagents for Organic Synthesis', this is a must-have resource for all synthetic chemists working in drug development and medicinal chemistry. For the selection the Editor focussed on three key synthetic approaches with the greatest impact: 1. Use of silicon as a "temporary tether" by unifying a reactive pair of functional groups and taking advantage of their template-biased intramolecular cyclization. 2. The specific use of the silane functionality as a hetero t-butyl group, often colloquially referred to as the use of silicon as a "fat proton". 3. The use of the Brook rearrangement as an "anion relay stratagem". A new feature in this Handbook is the reagent finder, an alphabetically organized lookup table arranged by organic functionality and specific structure of the silicon atom to which it is bound.

Author Biography

Philip Fuchs began his career at Purdue in 1973. Since that time, he has graduated an extended family of 55 Ph.D.s. His awards and honors include an Eli Lilly young faculty fellowship (1975), an Alfred P. Sloan fellowship (1977), a Pioneer in Laboratory Robotics award (1986), a Martin teaching award (1991), and being voted by the students as one of Top 10 Teachers in School of Science at Purdue (1991, 1993, 1995, 1996).
Fuchs has consulted for Pfizer, and Eli Lilly, served on the editorial board of The Journal of Organic Chemistry, and is currently an executive editor for the Electronic Encyclopedia of Organic Reagents (e-EROS), an online dynamic encyclopedia published by John Wiley & Sons.

Table of Contents

Prefacep. xiii
Introductionp. xv
Reagent Finder Tablep. xxiii
Short Note on InChIs and InChIKeysp. xxxi
3-Acetoxy-2-trimethylsilylmethyl-1-propenep. 1
Allyl(2-chloroethyl)dimethylsilanep. 9
Allyl Trichlorosilanep. 10
Allyltrimethylsilanep. 14
Allyltrimethylsilylzinc Chloridep. 24
Ammonium Hexafluorosilicatep. 25
Azidotrimethylsilanep. 26
Benzene, [[Difluoro(trimethylsilyl)methyl]seleno]p. 33
Benzene, [[Difluoro(trimethylsilyl)methyl]thio]-p. 36
Benzene, [[(1E)-2-(Trimethylsilyl)ethenyl]seleno]p. 39
Benzene, [[(1E)-2-trimethylsilyl)ethenyl]sulfonyl]-p. 42
2,1-Benzoxasilole, 1,3-Dihydro-1,1-dimethyl-p. 43
N-Benzyl-N-(methoxymethyl)-Ntrimethylsilylmethylaminep. 44
1,2-Bis(t-butyldimethylsilyl)hydrazinep. 46
1,2-Bis(chlorodimethylsilyl)ethanep. 48
1,4-Bis(dimethylamino)-1,1,4,4-tetramethyldisilethylenep. 50
Bis(1-methoxy-2-methyl-1-propenyloxy)dimethylsilanep. 51
Bis(methylthio)(trimethylsilyl)methanep. 52
[Bis(2-pyridyldimethylsilyl)methyl]lithiump. 54
1,3-Bis(triisopropylsilyl)propynep. 56
N,O-Bis(trimethylsilyl)acetamidep. 58
(1E,3E)-1,4-Bis(trimethylsilyl)-1,3-butadienep. 73
Bis(ß-trimethylsilylethanesulfonyl)imidep. 74
N,O-Bis(trimethylsilyl)hydroxylaminep. 75
Bis[(trimethylsilyl)methyl]zincp. 76
Bis(trimethylsilyl) Peroxidep. 79
Bis(trimethylsilyl) Selenidep. 82
Bis(trimethylsilyl) Sulfidep. 83
Bromomagnesium Hexamethyldisilazidep. 85
(Bromomethyl)chlorodimethylsilanep. 85
Bromotrimethylsilane 92, E)-1-Bromo-4-trimethylsilyl-1-buten-3-yne 100, Z)-2-Bromo-1-(trimethylsilyloxy)ethylenep. 105
2-Bromo-3-trimethylsilyl-1-propenep. 106
(1-Bromovinyl)trimethylsilanep. 109
t-Butyldimethylchlorosilanep. 110
t-Butyldimethylsilyl Cyanide 120 t-Butyldimethylsilyl)diphenylphosphinep. 121
2-t-Butyldimethylsilyl-1,3-dithianep. 122
O-(t-Butyldimethylsilyl)hydroxylaminep. 124
N-(t-Butyldimethylsilyl)-N-methyltrifluoroacetamidep. 125
t-Butyldimethylsilyl Trifluoromethanesulfonatep. 127
t-Butyldiphenylchlorosilanep. 135
1-t-Butylthio-1-t-butyldimethyl-silyloxyethylenep. 138
1-t-Butylthio-1-t-butyldimethylsilyloxypropenep. 141
t-Butyl Trimethylsilylacetatep. 147
3-Butyn-2-ol, 4-(Trimethylsilyl)-p. 148
Chlorodiisopropylsilanep. 151
Chlorodimethylsilanep. 156
Chlorodimethylvinylsilanep. 157
Chlorodiphenylsilanep. 162
(Chloromethyl)dimethylphenylsilane 162 E)-(3-Chloro-1-methyl-1-propenyl)-trimethylsilanep. 166
1-Chloro-1-methylsiletanep. 166
Chlorotrimethylsilanep. 170
Chlorotriphenylsilanep. 182
Cyanotrimethylsilanep. 184
Diazo(trimethylsilyl)methyllithiump. 191
(Dibromomethyl)trimethylsilanep. 197
Di-t-butylchlorosilanep. 198
Di-t-butyldichlorosilanep. 201
trans-1,1-Di-t-butyl-2,3-dimethylsiliranep. 207
Di-t-butylsilyl Bis(trifluoromethanesulfonate)p. 209
Dichlorodiisopropylsilanep. 222
Dichlorodimethylsilanep. 228
1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxanep. 230
1,1-Dichloro-2,2,2-trimethyl-1-phenyldisilanep. 233
Dicyanodimethylsilanep. 234
1,2-Diethoxy-1,2-bis(trimethylsilyloxy)ethylenep. 235
N,N-Diethylaminodimethylsilanep. 237
Diethyl[dimethyl(phenyl)silyl]aluminump. 237
Diiododimethylsilanep. 238
Diisopropyl Chlorosilane, Polymer-supportedp. 240
Diisopropylsilyl Bis(trifluoromethanesulfonate)p. 241
Dilithium Cyanobis(dimethylphenylsilyl)-cuprate 248 a,a-Dimethylallyl)trimethylsilanep. 252
(2-Dimethylaminomethylphenyl)phenylsilanep. 253
Dimethyl(phenyl)silanep. 254
Dimethylphenylsilyllithiump. 255
1,1-Dimethylsilacyclobutanep. 261
Dimethylthexylsilyl Chloridep. 263
Dimethylthexylsilyl Trifluoromethanesulfonatep. 265
1,3,2-Dioxaborolane, 2-(Dimethylphenylsilyl)-4,4,5,5- tetramethyl-, 1,3,2-Dioxaborolane, 4,4,5,5-Tetramethyl- 2-(methyldiphenylsilyl)-, 1,3,2-Dioxaborolane, 4,4,5,5- Tetramethyl-2-(triphenylsilyl)-p. 270
Diphenyldifluorosilanep. 276
Disilane, 1,1,1,2,2,2-hexamethyl-p. 278
1-Ethoxy-1-(trimethylsilyloxy)cyclopropanep. 285
Ethoxy(trimethylsilyl)acetylenep. 289
Ethyl Lithio(trimethylsilyl)acetatep. 293
Ethyl (Methyldiphenylsilyl)acetatep. 295
Ethyl 2-(Methyldiphenylsilyl)propanoatep. 296
Ethyl Trimethylsilylacetatep. 297
Fluorosilicic Acidp. 301
Formamide, N-N,bis(trimethylsilyl)-p. 302
Hexachlorodisilanep. 309
Hexamethylcyclotrisiloxanep. 310
Hexamethyldisiloxanep. 313
Hexamethyldisilazanep. 317
(Iodoethynyl)trimethylsilanep. 321
(Iodomethyl)trimethylsilanep. 323
Iodotrimethylsilane 325 E)-1-Iodo-3-trimethylsilyl-2-butenep. 336
3-Iodo-2-trimethylsilylmethyl-1-propenep. 338
Isocyanatotrimethylsilanep. 339
Ketene t-Butyldimethylsilyl Methyl Acetalp. 341
3-Lithio-1-triisopropylsilyl-1-propynep. 347
Lithium N-Benzyltrimethylsilylamidep. 349
Lithium Bis[dimethyl(phenyl)silyl]cupratep. 350
Lithium Cyano(dimethylphenylsilyl)cupratep. 353
Lithium Hexamethyldisilazidep. 356
Methanamine, 1,1-Bis(trimethylsilyl)p. 369
Methanesulfonamide, 1,1,1-Trifluoro-N[(trifluoromethyl)sulfonyl]-N(trimethylsilyl)-p. 372
(Methoxymethyl)bis(trimethylsilyl)aminep. 374
1-Methoxy-2-methyl-1-(trimethylsilyloxy)propenep. 376
N-Methyl-N,O-bis(trimethylsilyl)-hydroxylaminep. 380
Methyldiphenylchlorosilanep. 381
(Methylthio)trimethylsilanep. 388
Methyltrichlorosilanep. 389
Methyl Trichlorosilyl Ketene Acetal (1)p. 393
Methyl 2-Trimethylsilylacrylatep. 396
1-Methyl-1-(trimethylsilyl)allenep. 397
2-Methyl-2-(trimethylsilyloxy)-3-pentanonep. 400
PDMS Thimblesp. 403
Phenylsilane-Cesium Fluoridep. 408
(2-Phenylsulfonylethyl)trimethylsilanep. 409
Phenylthiobis(trimethylsilyl)methanep. 411
(Phenylthiomethyl)trimethylsilanep. 412
(Phenylthio)trimethylsilanep. 414
1-(Phenylthio)-1-(trimethylsilyl)cyclopropanep. 418
1-Phenylthio-1-trimethylsilylethylenep. 419
2-(Phenylthio)-2-(trimethylsilyl)propanep. 420
Phenyl Trimethylsilyl Selenidep. 421
Phosphine, Tris(trimethylsilyl)-p. 422
Polymethylhydrosiloxanep. 427
Potassium Hexamethyldisilazidep. 432
(+)-9-(1S,2S-Pseudoephedrinyl)-(10R)-(trimethylsilyl)- 9-borabicyclo[3.3.2]decanep. 453
2-Pyridyldimethylsilanep. 457
Silane, 1,1-(Chloromethylene)bis[1,1,1]-trimethyl-p. 461
Silane, Chlorotri-2-propen-1-yl-p. 463
Silane, 1,1-(1-Propene-1,3-diyl)bis[1,1,1-trimethyl-(E) Silane, 1,1-(1-Propene-1,3-diyl)bis[1,1,1-trimethyl-(Z) Silane, 1,1-(1-Propene-1,3-diyl)bis[1,1,1- trimethyl-(E + Z)p. 464
Sodium Hexamethyldisilazidep. 468
Tetrabutylammonium Difluorotriphenylsilicatep. 479
2,4,6,8-Tetraethenyl-2,4,6,8-tetramethylcyclotetrasiloxanep. 484
3-Tetrahydropyranyloxy-1-trimethylsilyl-1-propynep. 487
1,1,3,3-Tetramethyldisilazanep. 488
1,1,2,2-Tetraphenyldisilanep. 490
Trialkylsilyl Cyanide, Polymer-supportedp. 494
Tribenzylchlorosilanep. 496
Tri(t-butoxy)silanethiol 497 E)-1-Tri-n-butylstannyl-2-trimethylsilylethylenep. 499
Trichloroiodosilanep. 500
Triethoxysilanep. 501
Triethylsilanep. 506
Triethylsilyl Hydrotrioxidep. 514
3-Triethylsilyloxy-1,4-pentadiene 515 a-Triethylsilyl)propionaldehyde Cyclohexyliminep. 516
Triethylsilyl Trifluoromethanesulfonatep. 517
Trimethylsilyl Trifluoromethanesulfonatep. 518
Trifluoromethanesulfonic Acid, Chlorobis (1,1-Dimethylethyl)silyl Esterp. 537
Trifluoromethyltrimethylsilanep. 539
Triisopropylsilanethiolp. 546
(Triisopropylsilyl)acetylenep. 550
Triisopropylsilyl Chloridep. 554
Triisopropylsilylethynyl Triflonep. 558
Triisopropylsilyl Trifluoromethanesulfonatep. 559
Trimethylsilylacetic Acidp. 562
Trimethylsilylacetonep. 563
Trimethylsilylacetonitrilep. 564
Trimethylsilylacetylenep. 569
(Trimethylsilyl)allenep. 580
Trimethylsilylallyllithium 582 E)-1-Trimethylsilyl-1,3-butadienep. 585
3-Trimethylsilyl-3-buten-2-onep. 586
9-[1-(Trimethylsilyl)-2(E)-butenyl] -9-borabicyclo[3.3.1]nonanep. 588
Trimethylsilylcopperp. 589
Trimethylsilyldiazomethanep. 590
Trimethylsilyldiethylaminep. 598
2-Trimethylsilyl-1,3-dithianep. 604
2-(Trimethylsilyl)ethanesulfonamidep. 609
ß-Trimethylsilylethanesulfonyl Chloridep. 611
[N-(2-(Trimethylsilyl)ethanesulfonyl)-imino]phenyliodanep. 617
2-(Trimethylsilyl)ethanethiolp. 618
2-(Trimethylsilyl)ethanolp. 622
2-(Trimethylsilyl)ethoxycarbonylimidazolep. 627
2-(Trimethylsilyl)ethoxymethyl Chloridep. 628
[2-(Trimethylsilyl)ethoxymethyl]triphenylphosphonium Chloridep. 633
2-(Trimethylsilyl)ethyl Chloroformatep. 634
2-(Trimethylsilyl)ethyl 3-Nitro-1H-1,2,4-triazole-1-carboxylatep. 636
(Trimethylsilyl)ethynylcopper(I)p. 637
Trimethylsilyl Fluorosulfonyldifluoroacetatep. 638
N-(Trimethylsilyl)imidazolep. 640
Trimethylsilylketenep. 645
Trimethylsilyllithiump. 650
Trimethylsilyl Methanenitronatep. 653
1-Trimethylsilyl-1-methoxyallenep. 656
Trimethylsilylmethyl Azidep. 657
1-[(Trimethylsilyl)methyl]-1H-benzotriazolep. 658
2-Trimethylsilylmethyl-1,3-butadienep. 660
3-[(Trimethylsilyl)methyl]-3-butenoic Acid Methyl Esterp. 662
Trimethylsilylmethyllithiump. 664
Trimethylsilylmethylmagnesium Chloridep. 666
Trimethylsilylmethylpotassiump. 674
2-Trimethylsilylmethyl-2-propen-1-olp. 675
1-Trimethylsilyloxy-1,3-butadienep. 677
2-Trimethylsilyloxy-1,3-butadienep. 681
2-Trimethylsilyloxyfuran 684 Z)-2-(Trimethylsilyloxy)vinyllithiump. 693
5-Trimethylsilyl-1,3-pentadienep. 695
2-(Trimethylsilyl)phenyl Triflatep. 697
Trimethylsilylpotassiump. 700
2-Trimethylsilyl-1,3-propanediolp. 701
3-Trimethylsilyl-2-propen-1-yl Acetatep. 703
3-Trimethylsilyl-1-propynep. 704
3-Trimethylsilyl-2-propynylcopper(I)p. 711
2-(Trimethylsilyl)thiazolep. 712
Trimethylsilyltributylstannanep. 719
3-Trimethylsilyl-3-trimethylsilyloxy-1-propene 723 E)-1-Trimethylsilyl-2-trimethylstannylethylenep. 724
(Trimethylsilyl)vinylketenep. 725
1-(Trimethylsilyl)vinyllithium 726 E)-2-(Trimethylsilyl)vinyllithiump. 729
1-(Trimethylsilyl)vinylmagnesium Bromide-Copper(I) Iodidep. 730
Trimethyl{2-[(tributylstannyl)methyl]-2-propenyl}silanep. 731
Triphenylsilanep. 733
Tris(dimethylamino)sulfonium Difluorotrimethylsilicatep. 739
Tris(trimethylsilyl)aluminump. 745
Tris(trimethylsilyl)methanep. 746
Tris(trimethylsilyl)silanep. 747
Vinyltrimethylsilanep. 755
List of Contributorsp. 763
Reagent Formula Indexp. 779
Subject Index 785 ???
Table of Contents provided by Publisher. All Rights Reserved.

An electronic version of this book is available through VitalSource.

This book is viewable on PC, Mac, iPhone, iPad, iPod Touch, and most smartphones.

By purchasing, you will be able to view this book online, as well as download it, for the chosen number of days.

Digital License

You are licensing a digital product for a set duration. Durations are set forth in the product description, with "Lifetime" typically meaning five (5) years of online access and permanent download to a supported device. All licenses are non-transferable.

More details can be found here.

A downloadable version of this book is available through the eCampus Reader or compatible Adobe readers.

Applications are available on iOS, Android, PC, Mac, and Windows Mobile platforms.

Please view the compatibility matrix prior to purchase.