159087-44-2

Upstream product

• 16520-62-0 4-Phenyl-1-butyne 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Downstream Products

• 178693-08-8 ((CH₃)4C₂O₂BCCH(CH₂)2C₆H₅)2 
• 178693-14-6 (CH₃)4C₂O₂BCHC((CH₂)2C₆H₅)C(BO₂C₂(CH₃)4)CH(CH₂)2C₆H₅ 
• 178693-15-7 ((CH₃)4C₂O₂BCHC((CH₂)2C₆H₅))2 

Relevant academic research and scientific papers

The Pauson-Khand reaction using alkynylboronic esters: Solving a long-standing regioselectivity issue

The first intermolecular Pauson-Khand reaction, conducted using internal alkynylboronic esters, allows the installation of the boronic ester moiety at the β-position of the cyclopentenone with total regio- and stereoselectivity.

Synthesis of Triborylalkenes from Terminal Alkynes by Iridium-Catalyzed Tandem C-H Borylation and Diboration

A two-step reaction to convert terminal alkynes into triborylalkenes is reported. In the first step, the terminal alkyne and pinacolborane (HBpin) are converted into an alkynylboronate, which is catalyzed by an iridium complex supported by a SiNN pincer l

Catalytic dehydrogenative borylation of terminal alkynes by a SiNN pincer complex of iridium

Compounds with carbon-boron bonds are versatile intermediates for building more complex molecules via the elaboration of the carbon-boron bonds into other carbon-element bonds. The synthesis of carbon-boron bonds by catalytic dehydrogenative borylation of carbon-hydrogen bonds with dialkoxyboranes (RO)2BH is particularly attractive. It has been demonstrated for a variety of carbon-hydrogen bond types but not for the C(sp)-H bonds of terminal alkynes, for which hydroboration of the triple bond is a competing process. We report a new iridium catalyst that is strictly chemoselective for C-H borylation of terminal alkynes. The key to the success of this catalyst appears to be the new ancillary SiNN pincer ligand that combines amido, quinoline, and silyl donors and gives rise to structurally unusual Ir complexes. A variety of terminal alkynes (RC≡C-H) can be converted to their alkynylboronates (RC≡C-Bpin, where pin = pinacolate) in high yield and purity within minutes at ambient temperature.