4885-07-8Relevant articles and documents
A Chan-Evans-Lam approach to trisubstituted vinyl ethers
Molder, Bryce A.,Sader, Jonathan K.,Wulff, Jeremy E.
supporting information, p. 9649 - 9653 (2021/12/01)
Trisubstituted vinyl ethers were accessedviaChan-Evans-Lam coupling of vinyl trifluoroborates and primary aliphatic alcohols. This approach complements prior methods that required the use of neat liquid alcohol coupling partners. A palladium-catalyzed redox-relay Heck reaction was used to convert several vinyl ethers into aldehyde-functionalized 1,3-dihydroisobenzofurans.
Palladium-catalyzed methylation of alkynyl C(sp)-H bonds with dimethyl sulfonium ylides
Liu, Yan-Yun,Yang, Xu-Heng,Huang, Xiao-Cheng,Wei, Wen-Ting,Song, Ren-Jie,Li, Jin-Heng
, p. 10421 - 10426 (2013/11/06)
A novel palladium-catalyzed methylation protocol for the synthesis of methyl-functionalized internal alkynes has been established. This methylation method is achieved through a C(sp)-C(sp3) bond formation process and represents a new synthetic application of sulfonium ylides.
Indium-mediated allenylation of aldehydes and its application in carbohydrate chemistry: Efficient synthesis of D -ribulose and 1-deoxy- D -ribulose
Fischer, Michael,Schmoelzer, Christoph,Nowikow, Christina,Schmid, Walther
supporting information; experimental part, p. 1645 - 1651 (2011/05/05)
A two-step reaction sequence starting with the indium-mediated allenylation of aldehydes with 4-bromo-2-butyn-1-ols and subsequent ozonolysis of the resulting allenylic product was developed to generate a variety of dihydroxyacetone derivatives. The regioselectivity of the indium-promoted C-C bond-forming reaction can be manipulated through hydroxy protecting groups on 4-bromo-2-butyn-1-ol, yielding either allenes or alkynes as preferred products. Compared to established protocols, the necessary amount of indium for this type of allenylation can be decreased by a factor of two to four. The versatility of this strategy was demonstrated in thestereoselective and straightforward synthesis of D-ribulose and 1-deoxy-D-ribulose. Copyright