796104-41-1Relevant academic research and scientific papers
Dehydrative Allylation of Alkenyl sp2C-H Bonds
Cai, Xinying,Xing, Huicong,Qiu, Ju,Li, Bowen,Xie, Peizhong
supporting information, p. 4368 - 4373 (2021/05/26)
We designed a cooperative catalytic system by combining commercially available Ca(NTf2)PF6 and Pd(PPh3)4 to address the dehydrative allylation of alkenyl sp2 C-H bonds in an environmentally benign manner. A novel C-OH bond cleavage method was found to be crucial for this practical protocol. A variety of alkenes and allylic alcohols equipped with wide-spectrum functional groups can be successfully incorporated into the desired cross-coupling, affording 1,4-dienes with moderate to excellent yields and high stereo- and regioselectivity.
Reactivity of Stabilized Vinyldiazo Compounds toward Alkenyl- And Alkynylsilanes under Gold Catalysis: Regio- And Stereoselective Synthesis of Skipped Dienes and Enynes
Bernardo, Olaya,Yamamoto, Kota,Fernández, Israel,López, Luis A.
supporting information, p. 4452 - 4456 (2021/05/26)
We report the gold-catalyzed reaction of vinyldiazo compounds and alkenylsilanes to produce skipped dienes, which are common structural motifs in an array of bioactive compounds. This carbon-carbon bond-forming transformation proceeds with complete regio- and stereoselectivity with the silyl group serving as a regio- and stereocontrolling element. Likewise, the use of alkynylsilanes as reaction partners yielded skipped enynes resulting from a C(sp)-C(sp3) coupling. Mechanistic experiments and DFT studies have provided support for a stepwise mechanism.
Method for conversion of terminal alkenes to aldehydes using ruthenium(IV) porphyrin catalysts
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Page/Page column 3-4; sheet 7, (2008/06/13)
Aldehydes were obtained in excellent yields from ruthenium-porphyrin-catalyzed oxidation of various terminal alkenes with 2,6-dichloropyridine N-oxide under mild conditions. The aldehydes generated from these ruthenium-catalyzed alkene oxidation reactions can be used in-situ for olefination reactions with ethyl diazoacetate in the presence of PPh3, leading to one-pot diazoacetate olefination starting from alkenes.
Oxidative addition of N-halosuccinimides to palladium(0): The discovery of neutral palladium(II) imidate complexes, which enhance Stille coupling of allylic and benzylic halides
Crawforth, Catherine M.,Burling, Suzanne,Fairlamb, Ian J. S.,Kapdi, Anant R.,Taylor, Richard J. K.,Whitwood, Adrian C.
, p. 9736 - 9751 (2007/10/03)
The Stille coupling of organostannanes and organohalides, mediated by air and moisture stable palladium(II) phosphine complexes containing succinimide or phthalimide (imidate) ligands, has been investigated. An efficient synthetic route to several palladium(II) complexes containing succinimide and phthalimide ligands, has been developed. cis-Bromobis(triphenylphosphine)(N-succinimide) palladium(II) [(Ph3P)2Pd(N-Succ)Br] is shown to mediate the Stille coupling of allylic and benzylic halides with alkenyl, aryl and allyl stannanes. In competition experiments between 4-nitrobromobenzene and benzyl bromide with a cis-stannylvinyl ester, (Ph3P)2Pd(N-Succ)Br preferentially cross-couples benzyl bromide, whereas with other commonly employed precatalysts 4-nitrobromobenzene undergoes preferential cross-coupling. Furthermore, preferential reaction of deactivated benzyl bromides over activated benzyl bromides is observed for the first time. The type of halide and presence of a succinimide ligand are essential for effective Stille coupling. The type of phosphine ligand is also shown to alter the catalytic activity of palladium(II) succinimide complexes.
A practical and mild method for the highly selective conversion of terminal alkenes into aldehydes through epoxidation-isomerization with ruthenium(IV)-porphyrin catalysts
Chen, Jian,Che, Chi-Ming
, p. 4950 - 4954 (2007/10/03)
Aldehydes in excellent yields were obtained from the ruthenium-porphyrin- catalyzed oxidation of various terminal alkenes with 2,6-dichloropyridine N-oxide under mild conditions. The aldehydes generated from these ruthenium-catalyzed alkene oxidations can be used in situ for olefination reactions with ethyl diazoacetate in the presence of PPh3 in a one-pot diazoacetate olefination starting from alkenes (see example).
Bromobis(triphenylphosphine)(N-succinimide)palladium(II) as a novel catalyst for Stille cross-coupling reactions
Crawforth, Catherine M.,Burling, Suzanne,Fairlamb, Ian J. S.,Taylor, Richard J. K.,Whitwood, Adrian C.
, p. 2194 - 2195 (2007/10/03)
A new palladium catalyst is reported for Stille cross-coupling, namely [Pd(NCOC2H4CO)(PPh3)2Br].
Enantioselective Hydrolysis of Dialkyl 3-Monosubstituted Glutarates with Pig Liver Esterase: Structure-Optical Purity Relationships
Nakada, Masahisa,Kobayashi, Susumu,Ohno, Masaji,Iwasaki, Shigeo,Okuda, Shigenobu
, p. 3951 - 3954 (2007/10/02)
Dialkyl 3-monosubstituted glutarates are subjected to hydrolysis with pig liver esterase to afford the corresponding chiral half-esters.Synnthetically useful half-esters of higher optical purity are obtained from the prochiral substrates of more hydrophob
