38287-05-7Relevant academic research and scientific papers
Spectroscopic Characterization of Triplet 4,5-Benzocycloheptatrienylidene
Chateauneuf, John E.,Horn, Keith A.,Savino, Thomas G.
, p. 539 - 545 (1988)
4,5-Benzodiazocycloheptatriene (6) has been prepared by the low temperature nickel peroxide oxidation of the hydrazone of 4,5-benzotropone.Thermolysis of 6 in benzene produces 4,5-benzocycloheptatrienylidene (1) which undergoes a facile carbene-carbene re
Arylketones as Aryl Donors in Palladium-Catalyzed Suzuki-Miyaura Couplings
Wang, Zhen-Yu,Ma, Biao,Xu, Hui,Wang, Xing,Zhang, Xu,Dai, Hui-Xiong
, p. 8291 - 8295 (2021/11/13)
Herein, we report the arylation, alkylation, and alkenylation of aryl ketones via a palladium-catalyzed Suzuki-Miyaura cross-coupling reaction. The use of the pyridine-oxazoline ligand is the key to the cleavage of the unstrained C-C bond. The late-stage arylation of aryl ketones derived from drugs and natural products demonstrated the synthetic utility of this protocol.
Nickel-catalyzed cross-coupling of umpolung carbonyls and alkyl halides
Zhu, Dianhu,Lv, Leiyang,Qiu, Zihang,Li, Chao-Jun
, (2019/05/22)
An effective nickel-catalyzed cross-coupling of Umpolung carbonyls and alkyl halides was developed. Complementary to classical alkylation techniques, this reaction utilizes Umpolung carbonyls as the environmentally benign alkyl nucleophiles, providing an efficient and selective catalytic alternative to the traditional use of highly reactive alkyl organometallic reagents.
Nickel-Catalyzed Cross-Coupling of Umpolung Carbonyls and Alkyl Halides
Zhu, Dianhu,Lv, Leiyang,Qiu, Zihang,Li, Chao-Jun
, p. 6312 - 6322 (2019/05/24)
An effective nickel-catalyzed cross-coupling of Umpolung carbonyls and alkyl halides was developed. Complementary to classical alkylation techniques, this reaction utilizes Umpolung carbonyls as the environmentally benign alkyl nucleophiles, providing an efficient and selective catalytic alternative to the traditional use of highly reactive alkyl organometallic reagents.
Reductive coupling of benzyl oxalates with highly functionalized alkyl bromides by nickel catalysis
Yan, Xiao-Biao,Li, Chun-Ling,Jin, Wen-Jie,Guo, Peng,Shu, Xing-Zhong
, p. 4529 - 4534 (2018/05/28)
Coupling reactions involving non-sulfonated C-O electrophiles provide a promising method for forming C-C bonds, but the incorporation of functionalized or secondary alkyl groups remains a challenge due to the requirement for well-defined alkylmetal specie
1,3-dicyclohexylimidazol-2-ylidene as a superior ligand for the nickel-catalyzed cross-couplings of aryl and benzyl methyl ethers with organoboron reagents
Tobisu, Mamoru,Yasutome, Ayaka,Kinuta, Hirotaka,Nakamura, Keisuke,Chatani, Naoto
supporting information, p. 5572 - 5575 (2015/02/19)
A new catalytic system has been developed involving the use of Ni(cod)2 in conjunction with 1,3-dicyclohexylimidazol-2-ylidene for the cross-coupling of aryl and benzyl methyl ethers with organoboron reagents. This method not only allows for the use of readily available methyl ethers as halide surrogates but also provides a functional group tolerant method for the late-stage derivatization of complex molecules.
Photolysis of naphtho[b]cyclopropene. Detection of a diradical intermediate
Pan, Weitao,Jones Jr., Maitland,Esat, Burak,Lahti, Paul M.
, p. 1505 - 1508 (2007/10/03)
Photolysis of naphtho[b]cyclopropene in hydrocarbons leads to products derived from hydrogen abstraction by a diradical. Photolysis in a cryogenic matrix allows ESR detection of this diradical, which has zero field splitting parameters D/hc = 0.057, E/hc -1.
SPECTROSCOPIC CHARACTERIZATION OF 2-NAPHTHYLCARBENE
Horn, Keith A.,Chateauneuf, John E.
, p. 1465 - 1470 (2007/10/02)
The 308 nm excimer laser flash photolysis of 2-naphthyldiazomethane produces triplet 2-naphthylcarbene (λmax=362 nm) which decays with the observed pseudo-first-order rate constants (kexptl) of 5.54+/-0.03E6; 3.33+/-0.4E6; 1.64+/-0.02E7; and 3.05+/-0.4E6 s-1 in n-pentane, 2,2,4-trimethylpentane (2,2,4-TMP), benzene and Freon 113 respectively.In hydrocarbon solvents the observed decay of triplet 2-naphthylcarbene is correlated with the pseudo-first-order growth of the 2-naphthylmethyl radical (λmax=378 nm).Direct kinetic measurements of the reaction of triplet 2-naphthylcarbene in 2,2,4-TMP with cyclohexane, styrene, meth anol and carbon tetrachloride yielded bimolecular quenching rate constants of 1.48+/-0.04E6; 4.33+/-0.1E7; 7.25+/-0.5E6; and 3.35+/-0.07E6 M-1s-1.It is also found that 2-naphthylcarbene reacts with acetonitrile (kq=5.28+/-0.1E5 M-1s-1) to form a nitrile ylide intermediate with a λmax=372 nm.These results are interpreted in terms of a rapid singlet-triplet-2-naphthylcarbene equilibrium.
