DMAP-Accelerated Rhodium(I)
Chloride Catalyzed Hydroboration of Vinylarenes

Endo, Kohei; Hirokami, Munenao; Takeuchi, Kazunari; Shibata, Takanori

doi:10.1055/s-0028-1087415

Cited by 16 publications

(6 citation statements)

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“…[9] Yun and co-workers have described an enantioselective version of this highly regioselective hydroboration reaction, but we were able to employ CuCl in conjunction with a bis(diphenylphosphino)benzene (dppbz) ligand to accomplish the racemic reaction (see the Experimental and Supporting Information for further details). CO 2 was employed as the electrophile, as this readily available and inexpensive C1 source would lead to the formation of phenylacetic acids such as 2a .…”

Section: Resultsmentioning

confidence: 99%

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Beyond Benzyl Grignards: Facile Generation of Benzyl Carbanions from Styrenes

Grigg

Rigoli

Hoveln

et al. 2012

Chemistry A European J

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The facile generation of benzyl anion equivalents from styrenes has been achieved. A Cu-catalyzed hydroboration is used in conjunction with sterically-induced cleavage of the C-B bond with tBuOK. Quenching this reactive intermediate with heterocumulene electrophiles, including CO2, CS2, isocyanates and isothiocyanates, yields benzylic C-C bond formation. The utility of this methodology was demonstrated in a synthesis of the non-steroidal anti-inflammatory drug (+)-flurbiprofen.

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Section: Resultsmentioning

confidence: 99%

“…]9a],[12] The hydroboration was conducted using either toluene or THF as the solvent, then the reaction mixture was transferred via cannula to a solution of KO t Bu in THF at the appropriate temperature. Alternatively, the KO t Bu could be added to the hydroboration mixture to achieve a one-pot process.…”

Section: Resultsmentioning

confidence: 99%

Beyond Benzyl Grignards: Facile Generation of Benzyl Carbanions from Styrenes

Grigg

Rigoli

Hoveln

et al. 2012

Chemistry A European J

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“…The catalytic version of this reaction has been most welldeveloped with rhodium catalysts. [47][48][49][50][51][52][53][54][55][56][57][58][59][60] There is very little in the current literature regarding the use of platinum in hydroboration reactions. There is only one example of catechol borane being used in the hydroboration of a terminal alkene with a platinum catalyst.…”

Section: Hydroborationmentioning

confidence: 99%

Synthesis, Structure, and Catalytic Studies of Palladium and Platinum Bis-Sulfoxide Complexes

Drinkel

Linden

et al. 2013

Organometallics

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The bis-sulfoxide ligand p-tolyl-binaso and its derivatives can be used to synthesize neutral and cationic palladium and platinum complexes. Various Pt bis-sulfoxide complexes could be made by using the precursor Pt(M,SS,SS)-p-tolyl-binasoCl2 (5a) and abstracting the chlorides with silver salts. The Pd analogue of this compound (4) could not be used in the same way. In this case, the sulfoxides appear to be very weakly coordinated and different methods to make stable Pd bis-sulfoxide complexes had to be found. The nature of the bonding in the synthesized compounds was studied through analysis of their IR and NMR spectra and X-ray crystal structures. These studies revealed that the trans effect of other ligands in the complex is quite significant in determining the lability of the metal-sulfoxide bond. Some of the more stable platinum structures were then tested for their activity as catalysts in hydroboration and diboration reactions. AbstractThe bissulfoxide ligand, p-tolyl-binaso and its derivatives can be used to synthesize neutral and cationic palladium and platinum complexes. Various Pt bissulfoxide complexes could be made by using the precursor Pt{(M,S S ,S S )-p-tolyl-binaso}Cl 2 (5a) and abstracting the chlorides with silver salts. The Pd analogue of this compound (4) could not be used in the same way. In this case, the sulfoxides appear to be very weakly coordinated and different methods to make stable Pd bissulfoxide complexes had to be found. The nature of the bonding in the synthesized compounds was studied through analysis of their IR and NMR spectra and X-ray crystal structures. These studies revealed that the trans-effect of other ligands in the complex is quite significant in determining the lability of the metal-sulfoxide bond. Some of the more stable platinum structures were then tested for their activity as catalysts in hydroboration and diboration reactions.

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“…The discovery that certain transition metal complexes catalyze the addition of catecholborane (HBcat, cat = 1,2-O 2 C 6 H 4 ) or pinacolborane (HBpin, 1,2-O 2 C 2 Me 4 ) to unsaturated substrates has become an important strategy in organic synthesis [1][2][3][4][5][6][7][8]. Products obtained using a transition metal catalyzed hydroboration can have regio-, chemo-, or stereoselectivities complementary, or more remarkably, opposite to those from products obtained via the uncatalyzed route.…”

Section: Introductionmentioning

confidence: 99%