10289-45-9Relevant articles and documents
Iron-catalyzed cross-coupling reaction of alkyl halides with biphenyl grignard reagent
Dai,Liu,Zhang,Wei,Guan
, p. 6303 - 6305 (2013)
In the presence of a catalytic amount of iron salts and N,N,N',N'-tetramethylethylene diamine as additive, alkyl bromide reacted with biphenyl magnesium bromide to obtain the cross-coupling product in good yields. The suitable amount of catalyst and the additive are 5 % mol (based on alkyl bromide), 1.3 equiv(based on alkyl bromide), respectively. Under the optimal conditions, the yields of the crosscoupling could reach up to 92.3 %.
Iron fluoride/N-heterocyclic carbene catalyzed cross coupling between deactivated aryl chlorides and alkyl grignard reagents with or without β-hydrogens
Agata, Ryosuke,Iwamoto, Takahiro,Nakagawa, Naohisa,Isozaki, Katsuhiro,Hatakeyama, Takuji,Takaya, Hikaru,Nakamura, Masaharu
, p. 1733 - 1740 (2015)
High-yielding cross-coupling reactions of various combinations of aryl chlorides and alkyl Grignard reagents have been developed by using an iron(III) fluoride/1,3-bis(2,6-diisopropylphenyl)imidazolin-2-ylidene (SIPr) catalyst composite. The iron(III) fluoride/SIPr-catalyzed aryl-alkyl coupling demonstrates unprecedented scope for both aryl chlorides and alkyl Grignard reagents, thus enabling the first efficient coupling of electron-rich (deactivated) aryl chlorides with alkyl Grignard reagents without β-hydrogens. The present reaction is also effective for diverse alkyl Grignard reagents such as (trimethylsilyl)methyl, primary, and secondary alkyl Grignard reagents.
Synthesis method of 4-alkyl biphenylacetylene
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Paragraph 0045-0046, (2021/06/13)
The invention discloses a synthesis method of 4-alkyl biphenyl acetylene. The synthesis method comprises the following steps: carrying out catalytic hydrogenation reaction on 4-alkyl diketone to obtain 4-alkyl biphenyl; then reacting the 4-alkyl biphenyl with halogen to obtain 4-halogen-4 '-alkyl biphenyl; and allowing 4-halo-4 '-alkyl biphenyl and an ethynylation reagent to be subjected to a coupling reaction to obtain a compound shown in a formula (IV) under the action of alkali. The method creatively adopts a palladium catalyst and lewis acid combined catalytic system to carry out deoxidation reaction on 4-alkyl diketone, and has good selectivity and high yield; in addition, hydrogen is used as a hydrogen source, a byproduct is only water, and the method is environment-friendly.
Alkyl Carbagermatranes Enable Practical Palladium-Catalyzed sp2-sp3 Cross-Coupling
Xu, Meng-Yu,Jiang, Wei-Tao,Li, Ying,Xu, Qing-Hao,Zhou, Qiao-Lan,Yang, Shuo,Xiao, Bin
supporting information, p. 7582 - 7588 (2019/05/16)
Pd-catalyzed cross-coupling reactions have achieved tremendous accomplishments in the past decades. However, C(sp3)-hybridized nucleophiles generally remain as challenging coupling partners due to their sluggish transmetalation compared to the C(sp2)-hybridized counterparts. While a single-electron-transfer-based strategy using C(sp3)-hybridized nucleophiles had made significant progress recently, fewer breakthroughs have been made concerning the traditional two-electron mechanism involving C(sp3)-hybridized nucleophiles. In this report, we present a series of unique alkyl carbagermatranes that were proven to be highly reactive in cross-coupling reactions with our newly developed electron-deficient phosphine ligands. Generally, secondary alkyl carbagermatranes show slightly lower, yet comparable activity to its Sn analogue. Meanwhile, primary alkyl carbagermatranes exhibit high activity, and they were also proved stable enough to be compatible with various reactions. Chiral secondary benzyl carbagermatrane gave the coupling product under base/additive-free conditions with its configuration fully inversed, suggesting that transmetalation was carried out in an "SE2(open) Inv" pathway, which is consistent with Hiyama's previous observation. Notably, the cross-coupling of primary alkyl carbagermatranes could be performed under base/additive-free conditions with excellent functional group tolerance and therefore may have potentially important applications such as stapled peptide synthesis.
