863870-92-2Relevant articles and documents
Transition Metal-Free Synthesis of Halobenzo[b]furans from O-Aryl Carbamates via o-Lithiation Reactions
Feberero, Claudia,Renedo, Lorena,Sanz, Roberto,Sedano, Carlos,Suárez-Pantiga, Samuel,Virumbrales, Cintia
, (2022/01/24)
A straightforward and transition metal-free one-pot protocol to synthesize halobenzo[b]furans has been developed employing simple and easily available starting materials such as O-aryl carbamates and alkynylsulfones. The fine-tuning of the different steps involved was key to achieving a successful one-pot procedure. Initially, a directed ortho-lithiation process, which uses the carbamate as the directed metalation group, was crucial in providing access to O-2-alkynylaryl N,N-diethyl carbamates by a direct alkynylation of the o-lithiated carbamate, with arylsulfonylalkynes as electrophilic reagents. Cyclization of the generated o-alkynylaryl carbamates was successfully accomplished through a strategy involving in situ carbamate alkaline hydrolysis under conventional heating or microwave irradiation, coupled with a subsequent heterocyclization step delivering the desired benzo[b]furans. A wide variety of new halobenzo[b]furans has been synthesized and their utility has been demonstrated by their further transformation.
Twofold unsymmetrical C-H functionalization of PyrDipSi-substituted arenes: A general method for the synthesis of substituted meta-halophenols
Sarkar, Dhruba,Melkonyan, Ferdinand S.,Gulevich, Anton V.,Gevorgyan, Vladimir
, p. 10800 - 10804 (2013/10/22)
And the world is your oyster Sequential halogenation/oxygenation reactions of 2-diisopropylsilylpyrimidine-substituted arenes provide a general and efficient synthesis of substituted meta-halophenols from simple aryl iodides (see scheme; Piv=pivaloyl). The products are poised to undergo diverse C-C, C-N, and C-O bond-forming reactions that enable the transformation of their framework and the introduction of valuable functionalities. Copyright
A new and efficient synthesis of 4-functionalized benzo[6]furans from 2,3-dihalophenols
Sanz, Roberto,Castroviejo, M. Pilar,Fernandez, Yolanda,Fananas, Francisco J.
, p. 6548 - 6551 (2007/10/03)
Tandem Sonogashira coupling/5-endo-dig cyclization reactions on 2,3-dihalophenols suppose a straightforward entry to 4-halobenzo[b]furans, which can be easily transformed into 4-functionalized benzo[b]furans, that are difficult to synthesize by other proc
