67647-98-7Relevant academic research and scientific papers
SAMDI Mass Spectrometry-Enabled High-Throughput Optimization of a Traceless Petasis Reaction
Diagne, Abdallah B.,Li, Shuheng,Perkowski, Gregory A.,Mrksich, Milan,Thomson, Regan J.
supporting information, p. 658 - 662 (2015/11/17)
Development of the self-assembled monolayer/MALDI mass spectrometry (SAMDI) platform to enable a high-throughput optimization of a traceless Petasis reaction is described. More than 1800 unique reactions were conducted simultaneously on an array of self-assembled monolayers of alkanethiolates on gold to arrive at optimized conditions, which were then successfully transferred to the solution phase. The utility of this reaction was validated by the efficient synthesis of a variety of di- and trisubstituted allenes.
CuI-catalyzed cross-coupling of N-tosylhydrazones with terminal alkynes: Synthesis of 1,3-disubstituted allenes
Hossain, Mohammad Lokman,Ye, Fei,Zhang, Yan,Wang, Jianbo
, p. 1236 - 1241 (2013/04/10)
A CuI-catalyzed synthesis of 1,3-disubstituted allenes from 1-alkynes by the reaction with various N-tosylhydrazones has been developed. This method, which uses readily available starting materials and is operationally simple, offers 1,3-disubstituted all
C(sp)-C(sp3) bond formation through cu-catalyzed cross-coupling of N -tosylhydrazones and trialkylsilylethynes
Ye, Fei,Ma, Xiaoshen,Xiao, Qing,Li, Huan,Zhang, Yan,Wang, Jianbo
supporting information; experimental part, p. 5742 - 5745 (2012/05/07)
Copper-catalyzed cross-coupling of N-tosylhydrazones with trialkylsilylethynes leads to the formation of C(sp)-C(sp3) bonds. Cu carbene migratory insertion is proposed to play the key role in this transformation.
The synthesis of allenes by Cu(i)-catalyzed regio- and stereoselective reduction of propargylic carbonates with hydrosilanes
Zhong, Chongmin,Sasaki, Yusuke,Ito, Hajime,Sawamura, Masaya
supporting information; experimental part, p. 5850 - 5852 (2010/01/31)
Cu(i)-catalyzed anti-SN2′-type reduction of internal propargylic carbonates with hydrosilanes affords various di- and trisubstituted allenes with high regioselectivities; the reactions are compatible with functional groups and work efficiently
Synthesis of allenes by double Horner-Wadsworth-Emmons reaction
Inoue, Hideki,Tsubouchi, Hiroshi,Nagaoka, Yasuo,Tomioka, Kiyoshi
, p. 83 - 90 (2007/10/03)
LDA treatment of aldehydes or ketone with alkenylphosphonates 2, prepared by Horner-Wadsworth-Emmons (HWE) reaction of methylenebisphosphonate 1 with aldehydes, afforded Baylis-Hillman reaction-type products 5 in high yields. HWE olefination of 5 with KH or KH-18-crown-6 as a base provided allenes in good yields. One-flask procedure was successfully developed starting from 1 to afford an allene in a reasonably good yield.
Allenes through Horner-Wadsworth-Emmons olefination of alkenylphosphonates
Nagaoka, Yasuo,Inoue, Hideki,Tomioka, Kiyoshi
, p. 1843 - 1846 (2007/10/03)
Mono- and di-substituted allenes 5 were synthesized by successive Horner-Wadsworth-Emmons olefination starting from methylene-bisphosphonate 1 and two carbonyl compounds. The key to success is KH or KH-18-crown-6 as a base for the second HWE olefination o
