210964-23-1

Upstream product

• 5159-41-1 2-iodobenzyl alcohol 
• 74-99-7 prop-1-yne 
• 176910-65-9 2-(prop-1-yn-1-yl)benzaldehyde 

Downstream Products

• 442903-99-3 o-prop-1-ynylbenzyl bromide 
• 886862-07-3 2-(prop-1-ynyl)-benzyl 2-iodophenyl ether 
• 886862-09-5 2-(prop-1-ynyl)-benzyl 5-fluoro-2-iodophenyl ether 
• 350695-82-8 tert-butyl-dimethyl-(2-prop-1-ynyl-benzyloxy)-silane 
• 947395-75-7 1-(1-azido-methyl)-2-prop-1-ynyl-benzene 
• 886862-14-2 (Z)-3-[1-(3-fluoro-6H-dibenzo[b,e]oxepin-11-ylidene)-ethyl]-nitrobenzene 
• 886862-12-0 (Z)-3-[1-(6H-dibenzo[b,e]oxepin-11-ylidene)-ethyl]-nitrobenzene 
• 886862-23-3 3-[1-(6H-dibenzo[b,e]oxepin-11-ylidene)-ethyl]-phenylamine 

Relevant academic research and scientific papers

Fused-Ring Formation by an Intramolecular “Cut-and-Sew” Reaction between Cyclobutanones and Alkynes

The development of a catalytic intramolecular “cut-and-sew” transformation between cyclobutanones and alkynes to construct cyclohexenone-fused rings is described herein. The challenge arises from the need for selective coupling at the more sterically hind

Iodine-mediated electrophilic cyclization of 2-alkynyl-1-methylene azide aromatics leading to highly substituted isoquinolines and its application to the synthesis of norchelerythrine

The reaction of 2-alkynyl-1-methylene azide aromatics 1 with iodine and/or other iodium donors, such as the Barluenga reagent (Py2IBF 4/HBF4) and NIS, gave highly substituted cyclization products, namely, the 1,3-disubstituted 4-iodoisoquinolines 2, in good to high yields. Not only simple 2-alkynyl benzyl azides 1a-j and their substituted analogues 1k-u and 6 but also heteroaromatic analogues, including pyridine 8, pyrroles 10a-c, furane 10d, and thiophenes 10e-g, gave the corresponding isoquinoline derivatives in excellent to allowable yields. Electron-donating and electron-accepting substituents on the aromatic ring were equally tolerated, and either acidic or basic (or even neutral) reaction conditions, depending on the reactivity of the substrate, could be applied to smoothly convert the azide starting materials into the desired isoquinoline products in moderate to good yields. Limits were found only in connection with the substituent at the alkyne terminus, where electron-neutral or electron-donating substituents are clearly favored. The iodine-mediated electrophilic cyclization of 1 most probably proceeds through the iodonium ion intermediate 4 followed by nucleophilic cyclization of the azide and subsequent elimination of N2. This new methodology was successfully applied to the short synthesis of norchelerythrine.

Synthesis of 1,3,4-trisubstituted isoquinolines by iodine-mediated electrophilic cyclization of 2-alkynyl benzyl azides

(Chemical Equation Presented) The I's have it: A series of 2-alkynyl benzyl azides have been smoothly converted into 1,3,4-trisubstituted isoquinolines in moderate to excellent yields by an iodonium-mediated synthesis (see scheme). Depending on the struct

Cyclocarbopalladation of alkynes: A stereoselective method for preparing dibenzoxapine containing tetrasubstituted exocyclic alkenes

A palladium-catalyzed cascade carbometalation-cross coupling of alkyne route was developed for the preparation of tetrasubstituted exocyclic alkenes with high stereo- and regiocontrol. The effectiveness of this novel methodology was demonstrated by the sy

Studies on tellurium-containing heterocycles. Part 18. Preparation and structure of 2-benzotelluropyrylium salts and 2-benzoselenopyrylium salts

The regioselective and stereospecific intramolecular ring closure reactions of o-ethynylbenzyl tellurols 5A and o-ethynylbenzyl selenols 5B, which were readily generated by the reaction of the o-ethynylbenzyl bromides 4 with sodium hydrogen telluride (NaH

In situ generation of 1-propyne: A useful introduction of 1-propyne on unsaturated halogenated compounds through the sonogashira reaction

Reaction of (E/Z)-1-bromopropene with exactly 1.42 equivalents of nBuLi followed by addition of water produces in situ a THF solution of propyne. Addition of a vinylic or aromatic halogenated substrates, Pd(PPh3)2Cl2, CuI and an amine to this solution give high yield of the corresponding coupling product beating a propyne moiety. This practical procedure avoids the use of expensive and inflammable propyne gas which need a special apparatus for bubbling it into the reaction flask.