151416-94-3Relevant articles and documents
Platinum(0)-catalyzed diboration of alkynes
Ishiyama, Tatsuo,Matsuda, Nobuo,Miyaura, Norio,Suzuki, Akira
, p. 11018 - 11019 (1993)
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Platinum(0)-catalyzed diboration of alkynes with tetrakis(alkoxo)diborons: An efficient and convenient approach to cis-bis(boryl)alkenes
Ishiyama, Tatsuo,Matsuda, Nobuo,Murata, Miki,Ozawa, Fumiyuki,Suzuki, Akira,Miyaura, Norio
, p. 713 - 720 (1996)
Tetrakis(methoxo)- or bis(pinacolato)diboron [(RO)2BB(OR)2; (RO)2 = (MeO)2 (4a) and Me4C2O2 (1)] added to both terminal and internal alkynes in the presence of a catalytic amount of Pt(PPh3)4 to provide stereodefined cis-bis(boryl)alkenes (3) in excellent yields. Because reagents and reaction conditions were sufficiently mild, the procedure was readily extended to various functionalized alkynes. Mechanistic study revealed that the oxidative addition of bis(pinacolato)diboron (1) to Pt(PPh3)4 generates cis-Pt(BO2C2Me4)2(PPh 3)2 (5), whose structure was fully characterized by multinuclear NMR spectroscopies as well as single-crystal X-ray diffraction analysis. Complex 5 exhibited high reactivity for insertion to the alkyne giving 3 in high yields, thus implying that the oxidative addition of the B-B bond to a Pt(0) complex is an initial step in the platinum(0)-catalyzed diboration of alkynes.
One-pot synthesis of α,α-difluoroimines from alkynes through tandem catalytic diboration/fluorination/imination reaction
Ramírez, Jesús,Fernández, Elena
, p. 3841 - 3845 (2007)
Tandem catalytic diboration/fluorination/imination of arylacetylenes leads to the formation of α,α-difluoroimines, where the adjacent C{double bond, long}N and C-F2 bonds are formed simultaneously. The convenient one-pot protocol involves a Pt(0)-catalyzed diboration of terminal or internal arylalkynes followed by electrophilic fluorination with Selectfluor in the presence of primary amines and a dehydrating agent. A plausible mechanism for the three consecutive steps (diboration/fluorination/imination) is suggested in accordance with the electronic properties of the substrates. Alkynes/catalytic diboration/alkenyl diboronate esters/Selectfluor/electrophilic fluorination/α,α-difluoroimines.
Mixed Diboration of Alkynes Catalyzed by LiOH: Regio- and Stereoselective Synthesis of cis-1,2-Diborylalkenes
Peng, Sihan,Liu, Guixia,Huang, Zheng
, p. 7363 - 7366 (2018)
A diboration of terminal alkynes with an unsymmetrical diboron reagent pinBBdan has been achieved using LiOH as the catalyst in the presence of stoichiometric amounts of MeOH, affording 1,2-diborylalkenes with different boryl groups. The reaction proceeds in a highly regio- and stereoselective manner through cis-addition of pinBBdan to the C-C triple bond, with the Bdan moiety being incorporated at the internal position. By taking advantage of the different reactivities of the two boryl groups, the mixed diboration product can undergo the sequential, chemoselective cross-couplings with aryl bromides to form trisubstituted alkenes.
Dehydrogenative Diboration of Alkynes Catalyzed by Ir/CO/tBuNC System
Lai, Qingheng,Ozerov, Oleg V.
, (2020/11/30)
Catalytic dehydrogenative diboration (DHDB) of alkyne with HBpin was achieved using [Ir(COD)Cl]2 and other related Ir precursors under CO atmosphere. The selectivity for DHDB over hydroboration was higher in less polar solvents and under higher
Aggregation-induced emission molecular compound, preparation method and application thereof
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Paragraph 0120-0123, (2021/06/26)
The invention discloses an aggregation-induced emission molecular compound. The aggregation-induced emission molecular compound comprises a monosubstituted tetraphenyl ethylene derivative taking tetraphenyl ethylene as a skeleton, or a heavy atom-containi
Divergent and Stereoselective Synthesis of Tetraarylethylenes from Vinylboronates
Stang, Peter J.,Yao, Yisen,Zhang, Minghao,Zhao, Wanxiang
supporting information, p. 20090 - 20098 (2020/09/02)
The synthesis of a new tetraborylethylene (TBE) is reported, and its application in the preparation of [4+0]-tetraarylethenes (TAEs) is elucidated. TAEs have widespread applications in material science and supramolecular chemistry due to their aggregation-induced emission (AIE) properties. The divergent and stereoselective synthesis of [3+1]-, [2+2]-, and [2+1+1]-TAEs via multiple couplings of vinylboronates with aryl bromides is demonstrated. These couplings feature a broad substrate scope and excellent functional group compatibility due to mild reaction conditions. Facile access to various tetraarylethenes is provided. This strategy represents an important complement to the conventional methods employed for the synthesis of TAEs, and would be a valuable tool for synthesizing TAE-based molecules useful in functional materials, biological imaging and chemical sensing.
