Potassium Trifluoro(organo)borates: New Perspectives in Organic Chemistry

European Journal of Organic Chemistry - Tập 2003 Số 22 - Trang 4313-4327 - 2003
Sylvain Darses1, Jean‐Pierre Genet1
1Laboratoire de Synthèse Sélective Organique (UMR 7573, CNRS), Ecole Nationale Supérieure de Chimie de Paris, 11 rue P&M Curie, 75231 Paris cedex 05, France, Fax: (internat.) + 33‐1/44071062

Tóm tắt

AbstractPotassium trifluoro(organo)borates, highly stable organoboron derivatives, have recently emerged as promising alternatives to other organoboron reagents. These salts have shown interesting reactivity, not only through the intermediate formation of difluoroboranes, but also in transmetallation reactions with transition metals. In numerous reactions they have proven to be more reactive than boronic acids or esters. The preparation and reactivity of these ate complexes is discussed. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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Tài liệu tham khảo

I. Omae Applications of Organometallic Compounds Wiley Chichester 1998.

Metal‐Catalyzed Cross‐Coupling Reactions(Eds: F. Diederich P. J. Stang) Wiley‐VCH Weinheim 1998.

10.1021/ja01862a040

10.1021/ic50175a031

 

Chambers R. D., 1960, Prod. Chem. Soc., 114

10.1021/ja01505a007

 

10.1021/ja01493a014

Chambers R. D., 1960, Chem. Ind. (London), 76

10.1016/S0022-328X(00)81221-8

10.1016/S0022-328X(00)87855-9

 

10.1139/v63-113

S. L. Stafford M. Township M. County Patent US 3185730 May 25 1965.

10.1139/v70-649

10.1039/jr9650005144

10.1016/0022-328X(88)80020-2

10.1021/jo00115a016

10.1007/BF00602336

10.1021/ja983555r

10.1002/(SICI)1099-0690(199908)1999:8<1875::AID-EJOC1875>3.0.CO;2-W

Unpublished results from our laboratory.

10.1021/ol025845p

Reviews on organoboron compounds synthesis:

A. Pelter K. Smith H. C. Brown Borane Reagents Academic Press: London 1988.

D. S. Matteson Reactivity and Structure Concept in Organic Synthesis: Stereodirected Synthesis with Organoboranes; Springer 1994 vol. 32.

M. Vaultier B. Carboni Comprehensive Organometallic Chemistry(Eds.: G. Wilkinson F. G. A. Stone E. W. Abel) Pergamon: New York 1995 vol. 11 p. 191−276.

K. Smith A. Pelter Comprehensive Organic Synthesis(Eds.: B. M. Trost I. Fleming) Pergamon New York 1991 vol. 8 p. 703−731.

10.1016/S0022-328X(99)00690-7

10.1021/cr00104a001

10.1021/ol006896u

10.1021/ol025973d

Reviews on hydroboration:

10.1021/cr00006a003

10.1016/S0040-4020(97)00001-X

10.1021/ja0002823

10.1055/s-1997-3228

 

Rasset‐Deloge C., 1992, Bull. Soc. Chim. Fr., 129, 285

10.1016/S0040-4039(00)74099-8

10.1016/S0040-4039(98)01003-X

10.1021/ol0169729

10.1021/ja01501a029

10.1016/S0040-4020(01)80052-1

10.1021/om50004a008

10.1016/S0040-4020(98)00321-4

10.1021/jo0262356

 

Review: E. Negishi Comprehensive Organometallic Chemistry(Eds.: G. Wilkinson F. G. A. Stone E. W. Abel) Pergamon New York 1983 vol. 7 p. 337−347. Lithium alkynyltriisopropoxyborates have been shown to be stable at 0 °C in the absence of moisture for several months:

10.1016/0040-4039(88)85245-6

10.1016/S0040-4039(00)01543-4

10.1016/S0040-4039(99)00774-1

10.1055/s-2000-6303

10.1002/1521-3749(200101)627:1<15::AID-ZAAC15>3.0.CO;2-A

10.1002/1521-3749(200111)627:11<2499::AID-ZAAC2499>3.0.CO;2-Z

10.1002/1521-3749(200205)628:4<721::AID-ZAAC721>3.0.CO;2-9

10.1002/1521-3749(200205)628:4<883::AID-ZAAC883>3.0.CO;2-A

10.1016/S0040-4039(01)01983-9

10.1002/1521-3749(200205)628:4<723::AID-ZAAC723>3.0.CO;2-1

10.1021/jo016265t

10.1021/cr00022a010

D. S. Matteson Stereodirected Synthesis with Organoboranes Springer‐Verlag Berlin 1995.

10.1021/ol026619i

10.1016/S0040-4039(99)02273-X

For boronic Mannich reactions see:

10.1021/ja963178n

10.1021/ja981075u

10.1016/S0040-4039(00)02014-1

10.1021/cr941145p

10.1016/S0040-4039(00)00945-X

10.1016/S0040-4039(97)00939-8

For reviews concerning Miyaura‐Suzuki cross‐coupling reactions see:

10.1016/S0040-4020(02)01188-2

10.1021/cr00039a007

10.1021/cr020007u

For palladium‐catalyzed cross‐coupling of arenediazonium tetrafluoroborates with aryl‐ and alkenylboronic acids see:

10.1016/0040-4039(96)00699-5

Darses S., 1996, Bull. Soc. Chim. Fr., 133, 1095

10.1021/jo960058p

10.1021/jo9912451

10.1016/S0040-4039(00)01076-5

10.1021/ol016724c

10.1002/1521-3765(20020902)8:17<3901::AID-CHEM3901>3.0.CO;2-E

For the formation of arenediazonium tetrafluoroborates see:

Roe A., 1949, Org. Synth. Coll. Vol., 5, 193

H. Suschitzky Advances in Fluorine Chemistry Butterworths London 1965 vol. 4 pp. 1−30.

10.1021/jo01323a048

 

10.1002/anie.199518441

10.1002/anie.199518481

10.1016/S0022-1139(02)00157-4

10.1080/00397919908086252

10.1039/a900963i

10.1021/ja0002058

K. Puentener M. Scalon (Hoffmann‐La Roche AG) Patent EP1057831A2 May2000.

10.1021/jo026236y

10.1016/S0040-4039(02)01922-6

 

K. Sonogashira Comprehensive Organic Synthesis(Ed.: B. M. Trost) Pergamon Oxford 1991 vol. 3 p. 521.

N. Miyaura Cross‐coupling reactions. A practical guide Springer‐Verlag New York 2002.

Reviews:

10.1002/(SICI)1521-3773(19980817)37:15<2046::AID-ANIE2046>3.0.CO;2-L

10.1016/S0022-328X(98)01054-7

 

10.1016/S0040-4039(98)00503-6

10.1016/S0040-4039(98)00502-4

10.1021/ol034454n

Reviews:

10.1055/s-2001-10803

10.1016/S0040-4020(00)00618-9

For reviews on the rhodium‐catalyzed addition of organoboronic acids to unsaturated substrates:

10.1055/s-2001-14657

10.1021/ja012711i

10.1016/S0040-4039(02)01274-1

Amengual R., 2002, Synlett, 1791

10.1021/ja0261933

10.1021/ja0211095

10.1021/ol9910767

 

10.1016/S0040-4039(02)01288-1

10.1002/1099-0690(200211)2002:21<3552::AID-EJOC3552>3.0.CO;2-4

Results to be published.

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European Journal of Organic Chemistry

Tập 2003 Số 22

4313-4327

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