By Hans-Jorg Grutzmacher, Antonio Togni, Hansjörg Grützmacher
Catalytic heterofunctionalization is now a major region of analysis in homogeneous catalysis, permitting the formation of a large choice of bonds among carbon and different components by means of including compounds to alkenes and alkines. it's the catalysis of those key additions that makes this kind of synthesis so much effective.
In this primary guide at the topic, famous authors and editors current the entire smooth man made tools together with hydroamination, hydrosilylation, hydrozirconation, hydroalumination, hydroboration and
hydrophosphination.
An crucial 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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Additional info for Catalytic Heterofunctionalization
Example text
15] [15] [53] [53] [54] [55, 56] a) CH3CH(Ph)CH2Bcat (10%) and Ph(Me)CHCH(Bcat)2 (18%) was accompanied. The dehydrogenative coupling of borane is a very attractive method since the reaction directly yields (E)-1-alkenylboronates from alkenes (Table 1-5). However, the reaction can be limitedly applied to the synthesis of styrylboron derivatives [15, 53–56]. The reported procedures recommend a combination of vinylarene, a sterically hindered borane such as oxazaborolidine 4 or pinacolborane 2, and a phosphine-free rhodium(I) catalyst for achieving selective coupling.
Onak, Organoborane Chemistry, Academic, New York, 1975. (b) B. 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 mechanism involves an S-cis coordination of a diene to (PPh3)2Pt(Bpin)2 (92) by displacing two phosphines, insertion of the less-substituted double bond into the B–Pt bond giving anti-π-allyl(boryl)platinum(II), and finally reductive elimination of 102. Interestingly, a phosphine-free platinum(0) catalyst Pt(dba)2 (dba=dibenzalacetone) allows dimerization of the diene before the addition of diboron. Isoprene provides a 1,8-addition product (103) [136] having (E,E) configuration and a symmetrical structure derived from the head-to-head coupling.
