Dehydrogenative Diboration of Alkynes Catalyzed by Ir/CO/tBuNC System

被引:5
作者
Lai, Qingheng [1 ]
Ozerov, Oleg, V [1 ]
机构
[1] Texas A&M Univ, Dept Chem, 3255 TAMU, College Stn, TX 77842 USA
基金
美国国家科学基金会;
关键词
Iridium; catalysis; alkynes; diboration; hydroboration; C-H BORYLATION; CROSS-COUPLING REACTION; TERMINAL ALKYNES; STEREOSELECTIVE-SYNTHESIS; HYDRIDE COMPLEXES; REACTIVITY; RHODIUM(I); MECHANISM; EFFICIENT; COPPER;
D O I
10.1016/j.jorganchem.2020.121614
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
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 CO pressure. It was further improved when catalytic amount of tBuNC was added to the reaction. It was possible to achieve DHDB of both terminal and internal alkynes with selectivity for DHDB of up to 9:1 under the best conditions. Some DHDB products were isolated on the preparative scale. (C) 2020 Elsevier B.V. All rights reserved.
引用
收藏
页数:7
相关论文
共 49 条
[1]  
Ali H.A., 2002, ORGANOMETALLICS, V21, P4533
[2]  
Bjoern B., 2002, EUR J INORG CHEM, V10, P2569
[3]   Combined Experimental and Computational Studies of the Mechanism of Dehydrogenative Borylation of Terminal Alkynes Catalyzed by PNP Complexes of Iridium [J].
Foley, Bryan J. ;
Bhuvanesh, Nattamai ;
Zhou, Jia ;
Ozerov, Oleg, V .
ACS CATALYSIS, 2020, 10 (17) :9824-9836
[4]   Air- and Water -Tolerant (PNP)Ir Precatalyst for the Dehydrogenative Borylation of Terminal Alkynes [J].
Foley, Bryan J. ;
Ozerov, Oleg, V .
ORGANOMETALLICS, 2020, 39 (13) :2352-2355
[5]   THE SOLUBILITY OF HYDROGEN, OXYGEN, AND CARBON MONOXIDE IN SOME NON-POLAR SOLVENTS [J].
GJALDBAEK, JC .
ACTA CHEMICA SCANDINAVICA, 1952, 6 (05) :623-633
[6]   SYNTHESIS, CHARACTERIZATION, AND REACTIVITY OF ALKOXIDE AND HYDROXIDE COMPLEXES OF RHODIUM(I) AND IRIDIUM(I) [J].
GREEN, LM ;
MEEK, DW .
ORGANOMETALLICS, 1989, 8 (03) :659-666
[7]   Stereoselective Single (Copper) or Double (Platinum) Boronation of Alkynes Catalyzed by Magnesia-Supported Copper Oxide or Platinum Nanoparticles [J].
Grirrane, Abdessamad ;
Corma, Avelino ;
Garcia, Hermenegildo .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (08) :2467-2478
[8]   Rhodium-catalyzed hydroboration reactions with sulfur and nitrogen analogues of catecholborane [J].
Hadebe, Siphamandla W. ;
Robinson, Ross S. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (21) :4898-4904
[9]  
Herde J.L., 1974, INORG SYNTH, V15, P18
[10]   Ru-catalyzed isomerization of ω-alkenylboronates towards stereoselective synthesis of vinylboronates with subsequentin situfunctionalization [J].
Ho, Guo-Ming ;
Segura, Lucas ;
Marek, Ilan .
CHEMICAL SCIENCE, 2020, 11 (23) :5944-5949