138034-95-4

Upstream product

• 184370-64-7 (4-bromobut-3-yn-1-yl)benzene 
• 688-73-3 tri-n-butyl-tin hydride 
• 16520-62-0 4-Phenyl-1-butyne 
• 17955-46-3 trimethylsilyltributyltin 
• 104-53-0 3-phenyl-propionaldehyde 
• 218902-80-8 (4,4-diiodoobut-3-enyl)benzene 

Downstream Products

• 127208-56-4 9-phenyl-cis-1,6-nonadiene 

Relevant academic research and scientific papers

Illuminating Stannylation

We have developed photoboosted stannylation reactions of terminal alkynes (linear-selective hydrostannylation) and fluoroarenes (defluorostannylation), in which the stannyl anion is photoexcited to an excited triplet (T1) stannyl diradical species. This u

Stereoselective hydrogenolysis of 1,1-dibromo-1-alkenes and stereospecific synthesis of conjugated (Z)-alkenyl compounds

The Pd-catalyzed hydrogenolysis of 1,1-dibromoalkenes with Bu3SnH occurs at room temperature stereoselectively to give (Z)-1-bromo-1-alkenes. We sought to determine the optimal reaction conditions and illustrate the scope of this method with 32 dibromoalkenes including alkenyl- and alkynyl- conjugated 1,1-dibromo-1-alkenes 7a-h and 2,2-disubstituted 1,1-dibromo-1- alkenes 9af. Triphenylphosphine was the best ligand for the Pd-catalyzed hydrogenolysis. A wide range of solvents can be used for this reaction excluding EtOH, AcOH, and CHCl3. However, the reaction proceeds even in these solvents with the addition of a cosolvent or radical scavenger. The reaction of 1,1-diiodo-1-alkene (3) gave a mixture of (Z)-1-iodo-1-alkene (4), (Z)-1-tributylstannyl-1-alkene (5), and a terminal alkene 6, while that of 1,1-dichloroalkene did not occur. This selectivity can be explained by the stereoselective insertion of Pd(0) to a trans bromine-alkenyl carbon bond, successive transmetalation with Bu3SnH, and reductive elimination. The Suzuki and Sonogashira couplings of the resulting (Z)-1-bromo-1-alkenes with alkenyl(dialkoxy)borane and terminal alkyne occurred to give conjugated polyenes and enynes stereospecifically. The Pd-catalyzed hydrogenolysis of 1,1-dibromo-1-alkene and successive cross-coupling can be carried out either in a stepwise manner or in one-pot under the same Pd catalysis. These two processes should be useful for the synthesis of geometrically pure polyene and enyne with a Z-alkenyl unit.

Palladium-catalysed hydrostannylations of 1-bromoalkynes. A practical synthesis of (E)-1-stannylalk-1-enes

A practical synthesis of (E)-1-stannylalk-1-enes containing a range of oxygen and nitrogen functionality is highlighted, involving hydrostannylation followed by palladium-catalysed carbon-bromine bond cleavage reactions of 1-bromoalkynes.