120789-51-7Relevant articles and documents
Synthesis of 3-hydroxyalkylbenzo[b]furans via the palladium-catalysed heteroannulation of silyl-protected alkynols with 2-iodophenol
Bishop,Cottrell,Hands
, p. 1315 - 1320 (1997)
The palladium-catalysed annulation of silyl-protected alkynols with 2-iodophenol gives silyl-protected 3-hydroxyalkylbenzo[b]furans 3 a-l. The use of silyl-protected propynols bearing a free hydroxyl or an O-triethylsilyl protecting group resulted in the formation of 1-oxa-2-silacyclopent-3-enes 5a-d as the major products. Removal of the silyl protecting groups from silyl benzo[b]furans 3c, 3e and 3i affords 3-hydroxyalkylbenzo[b]furans 9a-c in good yield.
Palladium(0)-catalyzed rearrangement of silicon substituted vinyloxiranes. Enantiocontrolled preparation of α-tertiodutyldimethylsilyl-β,γ-unsaturated aldehydes
Gilloir, Fabienne,Malacria, Max
, p. 3859 - 3862 (1992)
Palladium(0)-catalyzed rearrangement of silicon substituted vinyloxiranes occured with a high stereoselectivity and in a very good chemical yield.
Synthesis and Isolation of Organogold Complexes through a Controlled 1,2-Silyl Migration
McGee, Philippe,Bellavance, Gabriel,Korobkov, Ilia,Tarasewicz, Anika,Barriault, Louis
, p. 9662 - 9665 (2015)
During our efforts toward the synthesis of naturally occurring polyprenylated polycyclic acylphloroglucinol using a AuI-catalyzed 6-endo dig carbocyclization, we isolated stable vinyllic gold intermediates. Optimization lead to isolated yields of up to 98 %, using 2-(di-tert-butylphosphino)biphenyl as the ligand. This transformation is derived from a silyl rearrangement that can be fully controlled according to the nature of the substituent on the ynone. This selective transformation does not require basic conditions to prevent protodeauration. These vinylgold complexes are the first isolated intermediates during a silyl migration with gold(I). More than 16 new organogold complexes were synthesized and characterized by single-crystal X-ray diffraction. Reactivity of these complexes is also presented.
Silyl-protected propargyl glycine for multiple labeling of peptides by chemoselective silyl-deprotection
Kamo, Naoki,Hayashi, Gosuke,Okamoto, Akimitsu
supporting information, (2021/05/03)
We synthesized Fmoc-propargyl glycine derivatives bearing different silyl protecting groups that can be readily introduced by using a standard solid-phase peptide coupling procedures. Taking advantage of the orthogonality between the different silyl prote
Direct Access to Allenylphosphine Oxides via a Metal Free Coupling of Propargylic Substrates with P(O)H Compounds
Yang, Chun-Hua,Fan, Huihui,Li, Huimin,Hou, Shenyin,Sun, Xiangkun,Luo, Donghao,Zhang, Yinchao,Yang, Zhantao,Chang, Junbiao
supporting information, p. 9438 - 9441 (2019/11/20)
A direct and convenient approach for the coupling of propargylic substrates with diphenylphosphine oxide in the presence of Tf2O and 2,6-lutidine has been developed. The method provides a general approach for the construction of attractive allenylphosphoryl skeletons with high atom and step economy under metal free conditions.
