197251-03-9Relevant academic research and scientific papers
Sodium-metal-promoted reductive 1,2-syn-diboration of alkynes with reduction-resistant trimethoxyborane
Fukazawa, Mizuki,Ito, Shiori,Nogi, Keisuke,Takahashi, Fumiya,Yorimitsu, Hideki
, p. 1171 - 1179 (2020/10/18)
Reductive 1,2-diboration of alkynes has been accomplished by means of sodium dispersion in the presence of trimethoxyborane as a reduction-resistant boron electrophile. Two boron moieties can be introduced onto alkynes with excellent syn selectivity to afford the corresponding (Z)-1,2-diborylalkenes. Bis(borate) species generated in situ can be involved in one-pot Suzuki-Miyaura arylation, formal arylboration of alkynes thus being executed.
Base-catalyzed diborylation of alkynes: synthesis and applications of cis-1,2-bis(boryl)alkenes
Kuang, Zhijie,Gao, Guoliang,Song, Qiuling
, p. 62 - 66 (2018/09/27)
An efficient, transition-metal free, and practical approach to cis-bis(boryl)alkenes from various alkynes was disclosed in the presence of a catalytic amount of K2CO3 under mild conditions. Meanwhile, tetrasubstituted alkenes and phenanthrene derivatives were readily constructed from the target diborylalkenes via Suzuki-Miyaura cross coupling.
Solvent-and ligand-free diboration of alkynes and alkenes catalyzed by platinum nanoparticles on titania
Alonso, Francisco,Moglie, Yanina,Pastor-Perez, Laura,Sepulveda-Escribano, Antonio
, p. 857 - 865 (2014/03/21)
Platinum nanoparticles supported on titania efficiently catalyzed the diboration of alkynes and alkenes under solvent-and ligand-free conditions in air. The cis-1,2-diborylalkenes and 1,2-diborylalkanes were obtained in moderate to excellent yields following, in most cases, a simple filtration workup protocol. The versatility of the cis-1,2-diboronvinyl compounds was demonstrated in a series of organic transformations, including the Suzuki-Miyaura cross coupling and the boron-halogen exchange. Click diboration: The diboration of alkynes and alkenes catalyzed by platinum nanoparticles on titania is shown to take place under solvent-and ligand-free conditions in air. The 1,2-diboronvinyl compounds are obtained with exclusive cis stereochemistry and are subjected to different useful chemical transformations.
Remarkable catalytic property of nanoporous gold on activation of diborons for direct diboration of alkynes
Chen, Qiang,Zhao, Jian,Ishikawa, Yoshifumi,Asao, Naoki,Yamamoto, Yoshinori,Jin, Tienan
supporting information, p. 5766 - 5769 (2013/12/04)
A novel catalytic property of nanoporous gold for activation of bis(pinacolato)diboron has been reported that allows the direct diboration of alkynes to proceed sufficiently in a heterogeneous process. The experimental results revealed that the nanoporous gold catalyst is able to cleave the B-B bond of bis(pinacolato)diboron without using any additives.
Copper-catalyzed borylation reactions of alkynes and arynes
Yoshida, Hiroto,Kawashima, Shota,Takemoto, Yuki,Okada, Kengo,Ohshita, Joji,Takaki, Ken
supporting information; experimental part, p. 235 - 238 (2012/02/16)
One, two, three, four: A copper(I)-phosphine complex catalyzes the diborylation of alkynes and arynes, and the tri- or tetraborylation of propargyl ethers (see scheme; pin=pinacolato). In the latter cases, the C-O bond(s) as well as the C≡C bond are borylated in one pot. Furthermore, a diborylation product serves as an intermediate in the efficient synthesis of ortho-terphenyls with pharmacological activity.
