125315-95-9

Upstream product

• 4250-82-2 (3,3-dimethyl-but-1-ynyl)benzene 
• 591-50-4 iodobenzene 
• 917-92-0 3,3-Dimethylbut-1-yne 
• 3846-66-0 β-tert-butylstyrene 
• 558-17-8 tert-Butyl iodide 
• 536-74-3 phenylacetylene 

Downstream Products

• 3740-05-4 (Z)-1-(3,3-dimethylbut-1-enyl)benzene 

Relevant academic research and scientific papers

Triethylborane Induced Stereoselective Radical Addition of R3SiH to Acetylenes and Stereoselective Reduction of Alkenyl Iodides with Tris(trimethylsilyl)silane

Triethylborane induced radical addition of various organosilanes (R3SiH) to acetylenes has been studied.Among them, tris(trimethylsilyl)silane (TTMSS) proved to be the best reagent for the hydrosilylation of acetylenic compounds in terms of yield and ster

Regio- And Stereoselective Hydroiodination of Internal Alkynes with Ex Situ-Generated HI

Herein, we report an efficient and practical hydroiodination of internal alkynes using HI generated ex situ from the readily available triethylsilane and I2. This system offers high regio- and stereoselectivity to afford (E)-vinyl iodides in good yields under mild conditions. Furthermore, the hydroiodination reaction shows high functional group tolerance toward alkyl, methoxy, halogen, trifluoromethyl, cyano, ester, halomethyl, acid-sensitive silyl ether, and acetal moieties.

Silver-catalyzed regioselective carbomagnesiation of alkynes with alkyl halides and Grignard reagents

A silver-catalyzed carbomagnesiation of alkynes with alkyl halides and Grignard reagents afforded alkenyl Grignard reagents regioselectively, where the alkyl group of the alkyl halide, but not that of the Grignard reagent, was introduced into the alkyne.

Surface-Mediated Reactions. 4. Hydrohalogenation of Alkynes

The use of appropriately prepared silica gel and alumina has been found to mediate the addition of hydrogen halides to alkynes.The technique has been rendered even more convenient by the use of various organic and inorganic acid halides that react in the presence of silica gel or alumina to generate hydrogen halides in situ.Treatment in this fashion of 1-propynylbenzene (1), which underwent no reaction in CH2Cl2 solution saturated with HCl, readily afforded the syn addition product, alkenyl chloride (E)-4a.On extended treatment (E)-4a underwent subsequent iaomerization to the thermodynamically more stable Z isomer.Thus either isomer of 4a could be obtained in good yield depending on the reaction conditions.In a similar way bromides (E)- and (Z)-4b were obtained without competing formation of the radical products (E)- and (Z)-5, which occurred in solution.In contrast with solution-phase hydroiodination of alkyne 1, which slowly afforded iodide (E)-4c, surface-mediated addition readily afforded (E)-4c, followed by isomerization to the Z isomer.E ->/- Z equilibration of the alkenyl halides 4 was shown to involve, at last in part, addition-elimination via the gem-dihalides 13.Analogous behavior was exhibited by the phenylalkynes 2 and 3 on surface-mediated hydrohalogenation.Surface-mediated addition of HBr and HI to the internal alkylalkyne 14 afforded principally the anti addition products (Z)-15b,c.Treatment of the terminal alkynes 17 and 22 with (COBr)2 over alumina gave the dibromides 20 and 24/25, respectively, whereas use of acetyl bromide as the HBr precursor afforded the alkenyl bromides 18b and 23.

IODINE ATOM TRANSFER ADDITION REACTIONS WITH ALKYNES. PART 1: ALKYL IODIDES

Simple 2*- and 3*- alkyl iodides add smoothly to electron deficient alkynes under standard atom transfer conditions (10percent Bu3SnSnBu3), sunlamp photolysis).Mechanistic experiments help to interpret stereochemical and yield trends, and a new model for

TRIETHYLBORANE-INDUCED RADICAL ADDITION OF ALKYL IODIDES TO ACETYLENES

Treatment of terminal acetylenes (R1CCH) with secondary or tertiary alkyl iodides (R2I) in the presence of triethylborane provides the corresponding alkenyl iodides (R1C(I)=CHR2) in good yields.