- Ni-Catalyzed Formal Cross-Electrophile Coupling of Alcohols with Aryl Halides
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Direct coupling of unactivated alcohols remains a challenge in current synthetic chemistry. We herein demonstrate a strategy building upon in situ halogenation/reductive coupling of alcohols with aryl halides to forge Csp2-Csp3 bonds. The combination of 2-chloro-3-ethylbenzo[d]oxazol-3-ium salt (CEBO) and TBAB as the mild bromination reagents enables rapid transformation of a wide range of alcohols to their bromide counterparts within one to 5 min in CH3CN and DMF, which is compatible with the Ni-catalyzed cross-electrophile coupling conditions in the presence of a chemical reductant. The present method is suitable for arylation of a myriad of structurally complex alcohols with no need for prepreparation of alkyl halides. More importantly, the mild and kinetically rapid bromination process has shown good selectivity in the bromination/arylation of symmetric diols and less sterically hindered hydroxyl groups in polyols, thus offering promise for selective functionalization of diols and polyols without laborious protecting/deprotecting operations. The practicality of this work is also evident in the arylation of a number of carbohydrates, drug compounds, and naturally occurring alcohols.
- Lin, Quan,Ma, Guobin,Gong, Hegui
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p. 14102 - 14109
(2021/11/20)
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- An alternative oxidising and brominating method converting alcohols to aldehydes and β-bromoethyl esters using ionic liquid [Bmim][Br3]
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[Bmim][Br3] is an oxidising reagent which converts alcohols into aldehydes and ketones in mild conditions and good yields; the use of the ionic liquid (IL) as both an oxidising and a brominating reagent in the one-pot synthesis of β-bromoethyl esters from benzyl alcohols and diols has also been studied.
- Zhang, Yu,Bao, Weiliang
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p. 263 - 266
(2007/10/03)
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- One-pot synthesis of ω-bromoesters from aromatic aldehydes and diols using pyridinium hydrobromide perbromide
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A simple and efficient one-pot procedure has been developed for the synthesis of ω-bromoesters from aromatic aldehydes and diols in the presence of pyridinium hydrobromide perbromide (PHPB) and triethoxymethane in which aldehyde reacts first with diol and the product, cyclic acetal, reacts with PHPB to give the final product, ω-bromoesters.
- Aoyama, Tadashi,Takido, Toshio,Kodomari, Mitsuo
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p. 1989 - 1992
(2007/10/03)
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- A new synthetic method for haloalkyl carboxylic esters from the radical ring cleavage of cyclic acetals with haloform
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A one-pot reaction of cyclic acetals with haloform catalyzed by AIBN(2,2'-azobisisobutyronitrile) provides a novel convenient way to prepare directly haloalkyl carboxylic esters in good yields.
- Hai-Xia, Lin,Liang-Heng, Xu,Nai-Ju, Huang
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p. 303 - 306
(2007/10/03)
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- PALLADIUM COMPLEX-CATALYZED CARBONYLATION OF ORGANIC HALIDES IN THE PRESENCE OF CYCLIC ETHERS: HALOHYDRIN ESTER SYNTHESIS
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Cyclic ethers were cleaved by palladium complex-catalyzed carbonylation of organic halides to give halohydrin esters.
- Tanaka, Masato,Koyanagi, Masayuki,Kobayashi, Toshiaki
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p. 3875 - 3878
(2007/10/02)
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