Selective Hydrogenation for Fine Chemicals: Recent Trends and New Developments

Advanced Synthesis and Catalysis - Tập 345 Số 1-2 - Trang 103-151 - 2003
Hans‐Ulrich Blaser1, Christophe Malan1, Benoı̂t Pugin1, Felix Spindler1, Heinz Steiner1, Martin Studer1
1Solvias AG, R 1055.628, P.O. Box, CH‐4002 Basel, Switzerland Fax: (+41)‐61‐686‐6311

Tóm tắt

AbstractIn this overview, recent trends and developments for the selective hydrogenation of multifunctional molecules are discussed and assessed from the point of view of fine chemicals synthesis. In a first part, the design and preparation of catalysts and ligands with interesting properties are summarized, particularly meant for the catalysis specialist. The following topics are described in some detail: How enantioselective homogeneous catalysts are designed and tested; new effective chiral monodentate phosphines; successful bidentate phosphines ligand families (with axially chiral biaryl‐ and ferrocenyl‐based backbones, new phospholanes and with stereogenic phosphorus); novel bidentate ligand families with P‐O and P‐N bonds; and oxazoline‐based ligands. A short overview on immobilized chiral complexes and of the toolbox of heterogeneous catalysis (bimetallic, colloidal and modified catalysts) concludes this chapter. In a second part, progress for selected catalytic transformations and generic selectivity problems is described, intended mainly for the organic chemist who has to solve specific synthetic problems. Emphasis is on the following topics: The enantioselective hydrogenation of olefins with various substitution patterns; the chemo‐ and enantioselective hydrogenation of ketones; the diastereo‐ and enantioselective hydrogenation of CN functions; the stereoselective hydrogenation of aromatic rings; chemoselectivity and hydroxylamine accumulation in the reduction of functionalized nitroarenes; chemoselectivity and new protecting groups for catalytic debenzylation; the mild hydrogenation of carboxylic acid derivatives; and the chemoselective hydrogenation of nitriles. In the last parts of the review, transfer hydrogenation and mechanistic issues are discussed, followed by a short conclusions and outlook paragraph.

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Tài liệu tham khảo

Rylander P. N., 1990, Hydrogenation Methods

Freifelder M., 1971, Practical Catalytic Hydrogenation

Nishimura S., 2001, Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis

See W. S. Knowles R. Noyori K. B. Sharpless Nobel Lectures Angew. Chem. Int. Ed.2002 41 1998–2022.

Machado R. M., 2001, Curr. Opinion Drug Discov. Devel., 4, 745

Brunner H., 1993, Handbook of Enantioselective Catalysis

Brown J. M., 1999, Comprehensive Asymmetric Catalysis., 121

10.1002/0471721506.ch1

10.1002/1521-3773(20020215)41:4<612::AID-ANIE612>3.0.CO;2-9

10.1021/ja016011p

10.1002/9783527618231.ch3e

10.1016/S0926-860X(01)00801-8

P. J.Harrington L. M.Hodges K.Puentener M.Scalone EP1127866 2001 assigned to Roche;

10.1021/op010005w

10.1039/c29710000481

10.1055/s-1992-21306

10.1021/ar990085c

10.1023/A:1013832630565

Knowles W. S., 1996, Chem. Ind. (Dekker), 68, 141

10.1021/ar00087a006

10.1002/1521-3773(20020617)41:12<1998::AID-ANIE1998>3.0.CO;2-8

10.1021/cr00013a005

Yamada I., 1997, J. Chem. Soc. Perkin Trans. 1, 1896

10.1002/1099-0682(200102)2001:2<327::AID-EJIC327>3.0.CO;2-A

Zhang X., 1999, Enantiomer, 4, 541

10.1021/jo990565h

10.1021/jo000066c

10.1002/1521-3773(20020503)41:9<1612::AID-ANIE1612>3.0.CO;2-H

10.1021/jo9824605

10.1002/(SICI)1521-3757(19990215)111:4<578::AID-ANGE578>3.0.CO;2-N

10.1002/(SICI)1521-3757(19980420)110:8<1203::AID-ANGE1203>3.0.CO;2-M

10.1021/cr00013a009

10.1248/cpb.33.5284

10.1246/bcsj.59.175

10.1111/j.1749-6632.1980.tb53625.x

10.1016/S0022-328X(97)00570-6

10.1021/ja0019373

10.1248/cpb.48.315

10.1002/1521-3773(20010401)40:7<1197::AID-ANIE1197>3.0.CO;2-G

10.1021/ja002507f

van denBerg A. J.Minnaard B. L.Feringa J. G.de Vries WO0204466 2000(assigned to DSM);

10.1016/S0957-4166(02)00096-4

J. G. de Vries personal communication; see also in this issue:

10.1002/adsc.200390026

10.1002/1521-3757(20020703)114:13<2454::AID-ANGE2454>3.0.CO;2-3

10.1039/b109827f

Claver C., 2000, Chem. Commun., 961

10.1002/1521-3773(20001103)39:21<3889::AID-ANIE3889>3.0.CO;2-T

10.1016/S0040-4039(00)01099-6

M. T.Reetz G.Mehler A.Meiswinkel WO0194278 2000(assigned to Studiengesellschaft Kohle mbH);

10.1016/S0040-4039(01)00319-7

10.1016/S0040-4039(01)01895-0

Agel F., 2002, Book of Abstracts, 13th ISHC, 51

B. Driessen‐Hölscher personal communication.

Huttenloch O., 2000, Chem. Eur. J., 6, 671

10.1002/1099-0682(20021)2002:1<199::AID-EJIC199>3.0.CO;2-H

B. Rieger Thesis University of Ulm 2002.

10.1021/ja00547a020

10.1002/1521-3773(20020617)41:12<2008::AID-ANIE2008>3.0.CO;2-4

10.1055/s-2001-14625

10.1016/S0040-4039(02)00383-0

10.1351/pac199668010131

10.1002/adsc.200390025

10.1002/1615-4169(20010330)343:3<264::AID-ADSC264>3.0.CO;2-T

Saito T., Proceedings ChiraSource2000

10.1021/jo000462v

10.1002/1521-3757(20010917)113:18<3533::AID-ANGE3533>3.0.CO;2-O

10.1021/ol991074m

10.1021/jo960211f

10.1021/jo015738t

10.1055/s-2001-18429

10.1021/ja000163n

10.1016/S0040-4039(02)00062-X

10.1002/1521-3773(20010105)40:1<40::AID-ANIE40>3.0.CO;2-5

10.1351/pac199971081493

10.1002/(SICI)1521-3773(19980703)37:12<1703::AID-ANIE1703>3.0.CO;2-I

10.1021/ja983257u

10.1021/ja026136

10.1021/ol000309n

10.1002/1521-3773(20001016)39:20<3707::AID-ANIE3707>3.0.CO;2-M

10.1021/ol0000814

Mechanism:

10.1021/ja991638h

10.1021/ja9906610

10.1039/a908098h

10.1002/1521-3773(20011001)40:19<3581::AID-ANIE3581>3.0.CO;2-7

10.1021/ja015902u

10.1021/ja001098k

10.1021/ol9904139

10.1021/ja026136

Hayashi T., 1995, Ferrocenes, 105

P.Herold S.Stutz T.Sturm W.Weissensteiner F.Spindler WO02/02500 2002(assigned to Speedel Pharma AG);

U.Berens patent submitted (assigned to Ciba SC/Solvias);

F. Spindler Solvias AG unpublished results.

10.2533/chimia.1999.275

10.2533/chimia.2001.688

Weissensteiner W., 2003, Adv. Synth. Catal., 346

Boaz N. W., 2002, Org. Lett., 4

10.1002/1521-3765(20020215)8:4<843::AID-CHEM843>3.0.CO;2-9

10.1016/S0040-4039(98)01832-2

10.1016/S0957-4166(99)00182-2

10.1016/S0957-4166(99)00002-6

10.1021/ja001271c

10.1246/bcsj.73.2571

10.1016/0957-4166(95)00330-R

10.1021/jo981939u

10.1021/jo9722717

10.1016/S0957-4166(98)00297-3

10.1039/a805524f

M. T.Reetz A.Gosberg WO0014096 1998(assigned to Studiengesellschaft Kohle MBH);

10.1021/ol0166193

10.1002/1521-3757(20000602)112:11<2057::AID-ANGE2057>3.0.CO;2-T

10.1002/(SICI)1521-3765(19990401)5:4<1160::AID-CHEM1160>3.0.CO;2-3

10.1021/cr990135r

overviews For, 1998, Synthesis, 1391

Maienza F., 2001, Chimia, 55, 694, 10.2533/chimia.2001.694

F. Maienza Thesis ETH Zürich 2001;

10.1021/om970539e

10.1021/om980754a

10.1021/jo010445l

J. Holz A. Monsees K. Drauz A. Börner personal communication;

10.1021/jo980960s

10.1016/S0040-4039(99)01458-6

10.1002/1099-0690(200112)2001:24<4615::AID-EJOC4615>3.0.CO;2-N

10.1039/b002994g

Nagel U., 1998, Z. Naturforsch., 53, 267, 10.1515/znb-1998-0301

10.1002/anie.199310521

10.1002/1615-4169(20010129)343:1<118::AID-ADSC118>3.0.CO;2-Z

10.1021/ja010161i

10.1016/S0957-4166(99)00431-0

10.1016/0040-4039(96)00967-7

10.1016/S0040-4039(00)00197-0

10.1021/jo9901182

10.1021/jo970884d

10.1021/jo001686g

10.1016/S0040-4039(98)02457-5

10.1021/ja970955q

10.1021/jo972268n

10.1039/b201976k

10.1021/ja020121u

10.1016/S0040-4039(00)02358-3

10.1021/ja974045k

10.1021/om0006312

10.1016/S0010-8545(98)00088-5

Carpentier J.‐F., 2003, Adv. Synth. Catal., 345

10.1016/S0957-4166(98)00423-6

10.1055/s-1998-1821

10.1016/S0957-4166(00)00092-6

10.1039/b007850f

10.1021/jo0157122

10.1016/S0957-4166(01)00464-5

10.1039/b109043g

10.1021/jo0255429

10.1021/jo015705d

10.1021/ar50141a005

10.1002/adsc.200390027

10.1002/chem.19970030609

10.1002/1615-4169(200107)343:5<450::AID-ADSC450>3.0.CO;2-7

10.1002/1521-3757(20011203)113:23<4577::AID-ANGE4577>3.0.CO;2-P

10.1002/1615-4169(200201)344:1<40::AID-ADSC40>3.0.CO;2-7

10.1021/jo001333h

10.1002/1521-3765(20011217)7:24<5391::AID-CHEM5391>3.0.CO;2-1

10.1016/S0040-4039(01)01041-3

10.1021/ja974095p

Zhang X., 2000, Proceedings of 2nd Symposium on New Synthetic Methods

10.1021/jo981612t

10.1021/jo0004613

10.1002/1521-3773(20020301)41:5<847::AID-ANIE847>3.0.CO;2-F

10.1021/ja00079a040

10.1021/ja00092a066

10.1021/jo00079a001

10.1016/S0040-4039(98)00842-9

10.1002/9783527613144.ch01

10.1002/1615-4169(20010430)343:4<369::AID-ADSC369>3.0.CO;2-3

10.1016/S0040-4039(01)00476-2

10.1016/S0040-4039(00)02035-9

10.1021/ja9837497

10.1002/1615-4169(200210)344:9<974::AID-ADSC974>3.0.CO;2-Z

10.1021/ja981137g

10.1002/masy.19940800112

10.1016/S0957-4166(02)00083-6

10.1039/a907187c

Augustine R. L., 2001, Chem. Ind. (Dekker), 82, 497

Brandts J. A. M., 2001, Chem. Ind. (Dekker), 82, 573

10.1016/S0022-328X(00)00127-3

10.1039/b003354p

10.1016/S0022-328X(00)00859-7

10.1002/pola.1212

Augustine R. L., 1996, Heterogeneous Catalysis for the Organic Chemist

Smith G. V., 1999, Heterogeneous Catalysis in Organic Chemistry

For more details see:

Blaser H.‐U., 1995, Modern Synthetic Methods, 181

Blaser H.‐U., 1998, Transition Metals for Organic Synthesis

10.1055/s-2001-14636

10.1002/adsc.200390029

10.1016/S1381-1169(00)00387-3

10.1016/S0920-5861(97)00026-6

10.1002/(SICI)1521-3773(19991216)38:24<3736::AID-ANIE3736>3.0.CO;2-E

10.1002/(SICI)1521-3765(20000218)6:4<618::AID-CHEM618>3.0.CO;2-A

10.1002/1615-4169(200206)344:3/4<266::AID-ADSC266>3.0.CO;2-O

10.1021/ic0109750

10.1039/a907193h

10.1016/S0040-4020(00)00771-7

10.1002/1521-3765(20000616)6:12<2200::AID-CHEM2200>3.0.CO;2-3

10.1021/jo015514a

10.1016/S0040-4020(98)00882-5

10.1016/S0040-4039(96)02309-X

Blaser H.‐U., 2001, Fine Chemicals through Heterogeneous Catalysis, 389

Baumeister P., 1998, Chem. Ind. (Dekker), 75, 207

10.1023/A:1019034128024

10.1023/A:1009050804228

10.1080/01614949808007106

10.1023/A:1019038820349

10.1016/S1566-7367(01)00052-8

von Arx M., 1999, Chimia., 53, 370

10.1039/b201542k

10.1021/ja983257u

10.1016/S0040-4020(99)01098-4

10.1080/00397919808007002

10.1002/1615-4169(200202)344:2<200::AID-ADSC200>3.0.CO;2-4

H.Steiner M.Benz H. P.Jalett M.Thommen WO‐A‐99/47486 1998 assigned to Ciba SC; see also

Rouhi A. M., 2002, Chem. Eng. News, 22

10.1002/(SICI)1099-0690(199804)1998:4<729::AID-EJOC729>3.0.CO;2-B

10.1016/S0920-5861(97)00010-2

10.1016/B978-0-08-092493-9.50015-3

10.1016/S0040-4039(98)02590-8

Blaser H.‐U., 1999, Comprehensive Asymmetric Catalysis, 247

10.1021/ol0002471

10.1021/ja003630

10.1021/om001054k

10.1021/jo990594s

10.1002/1615-4169(20010129)343:1<68::AID-ADSC68>3.0.CO;2-G

10.1016/S0022-328X(00)00766-X

10.1055/s-1999-3106

10.1016/S0957-4166(98)00451-0

10.1021/ja984309i

A. J.Blacker WO9842643B11997 (assigned to Avecia);

A. J. Blacker Chiral Europe'00 Scientific Update;

Blacker A. J., Proceedings of ChiraSource '01

10.1021/ol990098q

K.Tani T.Yamagata T.Yokozawa N.Sayo JP11 335334 1999(assigned to Takasago);

2000, Chem. Abst., 132, 22746u

10.1016/S0957-4166(98)00232-8

Donkervoort J. G., 2001, Fine Chemicals through Heterogeneous Catalysis, 407

10.1021/om980219a

10.1039/b005689h

10.1007/s007060070013

R.Fuchs EP0803502 A2 1997 assigned to Lonza AG.

10.1002/(SICI)1521-3765(20000317)6:6<949::AID-CHEM949>3.0.CO;2-H

10.1006/jcat.1999.2525

10.1023/A:1019077800901

10.1006/jcat.2002.3599

10.1016/S0926-860X(00)00795-X

10.1016/S0926-860X(00)00428-2

A. Tungler personal communication.

Steiner H., 2000, Topics in Catalysis

Burmeister R., 1995, Stud. Surf. Sci. Catal., 92, 343

Roessler F., 2000, Proceedings 12th International Congress on Catalysis

Hu T. Q., 1997, Can. J. Chem., 75, 1234, 10.1139/v97-149

10.1016/S1381-1169(01)00187-X

10.1246/cl.2000.428

10.1002/1521-3773(20020104)41:1<99::AID-ANIE99>3.0.CO;2-E

10.1016/S1381-1169(00)00533-1

10.1021/om990713u

10.1039/a606985a

10.1016/S0920-5861(97)00005-9

10.1016/S0926-860X(01)00910-3

10.1016/S0040-4020(99)01108-4

10.1021/ol005589l

10.1016/S0040-4039(96)02309-X

10.1016/S0040-4039(98)00961-7

10.1016/S0040-4039(00)01661-0

Yokoyama T., 2001, Fine Chemicals through Heterogeneous Catalysis, 370

10.1016/S0926-860X(01)00795-5

10.1002/1615-4169(20011231)343:8<802::AID-ADSC802>3.0.CO;2-T

S.Antons B.Beitzke EP696575 A1 assigned to Bayer AG 1996;

Chem. Abstr. 1996 125

10.1021/jo991112f

10.1016/0040-4039(94)02453-I

10.1016/S0022-328X(99)00038-8

10.1039/a801807c

10.1246/bcsj.74.1803

10.1080/01614949408009469

Allgeier A. M., 2001, Chem. Ind. (Dekker), 82, 229

Thomas‐Pryor S. N., 1998, Chem. Ind. (Dekker), 75, 195

Johnson T. A., 2001, Chem. Ind. (Dekker), 82, 201

O. G.Degischer F.Roessler EP1108469 2001 assigned to F. Hoffmann La Roche AG.

Tinapp P., 1980, Methoden der organischen Chemie, 111

10.1016/0926-860X(95)00039-9

Gaube Poepel. J., 1991, DECHEMA Monogr., 122, 189

10.1002/lipi.19910930301

10.1021/cr00066a003

Gladiali S., 1998, Transition Metals for Organic Synthesis

10.1021/cr00013a015

10.1021/ar9502341

10.1016/S0957-4166(99)00216-5

10.1021/om010960

10.1016/S0957-4166(00)00310-4

10.1039/b107822b

10.1021/ol990226a

10.1021/om990210o

10.1002/1521-3765(20010401)7:7<1431::AID-CHEM1431>3.0.CO;2-L

10.1039/a808170k

10.1002/1521-3765(20000804)6:15<2818::AID-CHEM2818>3.0.CO;2-Q

10.1351/pac200173020209

10.1016/S0926-860X(01)00825-0

10.1023/A:1013874202404

10.1006/jcat.1998.2338

10.1039/c39900000869

Brown J. M., 2000, Curr. Opinion Drug Discov. Devel., 3, 825

10.1021/jo010721w

10.1021/ja010982n

10.1021/om990482r

10.1021/ja0105257

10.1039/a908047c

10.1002/1615-4169(200206)344:3/4<221::AID-ADSC221>3.0.CO;2-N

10.1002/1615-4169(200206)344:3/4<239::AID-ADSC239>3.0.CO;2-O

10.1016/S0920-5861(01)00541-7

10.1039/b107270f

Tacke T., 1998, Chem. Ind (Dekker), 75, 345

10.1021/cr970090z

Bose A. K., 1996, Synlett, 575

10.1016/S0040-4039(01)00969-8

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Advanced Synthesis and Catalysis

Tập 345 Số 1-2

103-151

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