Catalytic Heterofunctionalization - download pdf or read online

By Hans-Jorg Grutzmacher, Antonio Togni, Hansjörg Grützmacher

ISBN-10: 3527302344

ISBN-13: 9783527302345

Catalytic heterofunctionalization is now a major quarter of study in homogeneous catalysis, permitting the formation of a wide selection of bonds among carbon and different parts by means of including compounds to alkenes and alkines. it's the catalysis of those key additions that makes this kind of synthesis such a lot effective.
In this primary instruction manual at the topic, famous authors and editors current the entire glossy man made equipment together with hydroamination, hydrosilylation, hydrozirconation, hydroalumination, hydroboration and
hydrophosphination.
An vital resource for each researcher and practitioner of homogeneous catalysis in addition to for all artificial natural chemists in academia and undefined.

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M. Mikhailov, Tu. N. , Amsterdam, 1983. (c) A. Pelter, K. Smith, H. C. Brown, Borane Reagents, Academic, New-York, 1988. (d) D. S. Matteson, Stereodirected Synthesis with Organoboranes, Springer, Berlin, 1995.

The boryl group is selectively introduced into the more reactive C≡CH rather than C=C for enynes and into the terminal C≡CH rather than the internal C≡CR for diynes, again suggesting a mechanism proceeding through the first insertion into the Pd–B bond in preference to the Pd–Sn or Pd–Si bond. X XB(NR2)2 (87 or 90) EtO2C EtO2C EtO2C EtO2C X=Me3Sn/PdCl2(PPh3)2/25 °C, 82% X=PhMe2Si/Pd2(dba)3-4etpo/110 °C, 84% B N Me Me N R (CH2)n R 90 (CH2)n PdCl2(PPh3)2 benzene/25 °C R=H R=H R=H R=Et Scheme 1-27 SnMe3 B(NR2)2 n=2, 97% n=3, 92% n=4, 84% n=3, 86% Carbocyclization of Diynes and Enynes The transformation of 1,2-bis(boryl)-1-alkenes via a cross-coupling reaction provides a method for regio- and stereoselective synthesis of 1-alkenylboranes because they have potential reactivity difference between two C–B bonds [125] (Scheme 128).

18 h OR Si P Si OR Ph CF3CO2H I PdCl2(dppf)/aq. t. / 18 h Et 57% Et Ph OR Tamoxifen (R=CH2CH2NMe2) Scheme 1-29 Solid-Phase Synthesis of Tamoxifen 27 28 1 Hydroboration, Diboration, Silylboration and Stannylboration R1 82 or 83 R1 R2 catalyst/rt/50 °C >B B< R2 (RO)2BB(OR)2 Alkene Catalyst pinB-Bpin (82) 1-decene styrene cyclopentene cyclohexene norbornene 1-hexene norbornene 4-MeOPhCH=CH2 styrene PhCH=CHPh Pt(dba)2/50°C Pt(dba)2/50°C Pt(dba)2/50°C Pt(dba)2/50°C Pt(dba)2/50°C Pt(cod)2rt Pt(cod)2rt AuCl(PEt3)-2dcpe/rt [(acac)Rh(dppm)]B2cat3/rt [(acac)Rh(dppm)]B2cat3/rt catB-Bcat (83) Yield/% 82 86 85 0 85 95 93 high 87 92-99 Ref.

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Catalytic Heterofunctionalization by Hans-Jorg Grutzmacher, Antonio Togni, Hansjörg Grützmacher


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