Highly efficient monophosphine platinum catalysts for alkyne diboration

Thomas, Rhodri Ll.; Souza, Fabio E. S.; Marder, Todd B.

doi:10.1039/b010225n

Cited by 120 publications

(59 citation statements)

References 71 publications

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“…These compounds have already been synthesized. [14,15] Compared with boranes, the use of boronic acids and boronates as reagents, particularly compound 2, is advantageous due to the simplicity of the manipulation and the convenient reaction protocol employing these compounds. Bis(pinacolato)diboron is considerably more stable towards oxygen and moisture than other borane analogues that cannot be handled in air due to oxidative and hydrolytic reactions of the B À H bonds.…”

Section: Introductionmentioning

confidence: 99%

Stereoselective Single (Copper) or Double (Platinum) Boronation of Alkynes Catalyzed by Magnesia‐Supported Copper Oxide or Platinum Nanoparticles

Grirrane

Corma

Garcı́a

2011

Chemistry A European J

107

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Copper(II) oxide nanoparticles supported on magnesia have been prepared from Cu(II) supported on magnesia by hydrogen reduction at 400 °C followed by storage under ambient conditions. X-ray photoelectron spectroscopy of the material clearly shows that immediately after the reduction copper(0)-metal nanoparticles are present on the magnesia support, but they undergo fast oxidation to copper oxide upon contact with the ambient for a short time. TEM images show that the catalytically active CuO/MgO material is formed of well-dispersed copper oxide nanoparticles supported on fibrous MgO. CuO/MgO exhibits a remarkable catalytic activity for the monoborylation of aromatic, aliphatic, terminal, and internal alkynes, the products being formed with high regio- (borylation at the less substituted carbon) and stereoselectivity (trans-configured). CuO/MgO exhibits complete chemoselectivity towards the monoborylation of alkynes in the presence of alkenes. Other metal nanoparticles such as gold or palladium are inactive towards borylation, but undergo undesirable oligomerization or partial hydrogenation of the C≡C triple bond. In contrast, platinum, either supported on magnesia or on nanoparticulate ceria, efficiently promotes the stereoselective diborylation of alkynes to yield a cis-configured diboronate alkene. By using platinum as the catalyst we have developed a tandem diborylation/hydrogenation reaction that gives vic-diboronated alkanes from alkynes in one pot.

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Section: Introductionmentioning

confidence: 99%

Stereoselective Single (Copper) or Double (Platinum) Boronation of Alkynes Catalyzed by Magnesia‐Supported Copper Oxide or Platinum Nanoparticles

Grirrane

Corma

Garcı́a

2011

Chemistry A European J

107

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“…A similar trend has been described in the diboration of para-substituted terminal phenylacetylenes with Pt(0) catalytic complexes where electron withdrawing substituents diminish the reaction rates. 15 Remarkably, the hindered internal alkene indene was able to be cleanly transformed to the desired product, although with a low conversion ( Table 1, …”

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confidence: 99%

Unprecedented use of silver(i) N-heterocyclic carbene complexes for the catalytic preparation of 1,2-bis(boronate) esters

et al. 2005

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“…[20][21][22]38 The proposed catalytic cycle 8,20-22 involves oxidative addition, insertion and reductive elimination processes. The reaction is accelerated significantly with an unsaturated platinum(0) complex having a donating phosphine ligand and is slowed down in the presence of PPh 3 added to Pt(PPh 3 ) 4 , thus suggesting a rate-determining role of both oxidative addition and phosphine dissociation (34 to 35).…”

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confidence: 99%

Metal-Catalyzed Reactions of Organoboronic Acids and Esters

Miyaura¹

2008

Bulletin of the Chemical Society of Japan

365

110

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Metal-catalyzed B-C and C-C bond-forming reactions of organoboronic acids that have been pursued in the past three decades by our group are summarized in this article. B-C bond-forming reactions for the synthesis of organoboronic acid derivatives include metal-catalyzed addition reactions of pinacolborane or catecholborane (hydroboration), bis(pinacolato)diboron (diboration), and alkylthioboranes (thioboration) to alkenes, alkynes, 1,3-alkadienes, or 1,2-alkadienes (allenes). Other B-C bond-forming reactions include coupling reactions of pinacolborane or bis(pinacolato)diboron for borylation of C-halogen bonds with palladium catalysts and C-H bonds of arenes and alkenes with iridium catalysts. These reactions have provided a convenient new access to aryl-, 1-alkenyl-, allyl-, or benzylboronates. Metal-catalyzed C-C and C-N bond-forming reactions using boronic acid derivatives include synthesis of novel cyclic triolborate salts for palladium-or copper-catalyzed cross-coupling reactions with organic halides or amines, rhodium-or palladiumcatalyzed 1,4-addition reactions of arylboronic acids to ,-unsaturated carbonyl compounds and rhodium-catalyzed addition of aryl-and 1-alkenylboronic acids to aldehydes and imines.

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Highly efficient monophosphine platinum catalysts for alkyne diboration

Cited by 120 publications

References 71 publications

Stereoselective Single (Copper) or Double (Platinum) Boronation of Alkynes Catalyzed by Magnesia‐Supported Copper Oxide or Platinum Nanoparticles

Stereoselective Single (Copper) or Double (Platinum) Boronation of Alkynes Catalyzed by Magnesia‐Supported Copper Oxide or Platinum Nanoparticles

Unprecedented use of silver(i) N-heterocyclic carbene complexes for the catalytic preparation of 1,2-bis(boronate) esters

Metal-Catalyzed Reactions of Organoboronic Acids and Esters

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