Ligand-free, catalytic and regioselective hydroboration of selenoalkynes

被引：9

作者：

Baldassari, Lucas L. ^{[1
]}

Santos, Kelvin S. ^{[1
]}

Ebersol, Camila P. ^{[1
]}

Ludtke, Diogo S. ^{[1
]}

Moro, Angelica, V ^{[1
]}

机构：

[1] Univ Fed Rio Grande do Sul, Inst Chem, Av Bento Goncalves 9500, BR-91501970 Porto Alegre, RS, Brazil

来源：

CATALYSIS SCIENCE & TECHNOLOGY | 2020年 / 10卷 / 22期

关键词：

STEREOSELECTIVE-SYNTHESIS; SELECTIVE HYDROBORATION; INTERNAL ALKYNES; FUNCTIONALIZED ALKYNES; FORMAL HYDROBORATION; SODIUM BOROHYDRIDE; COUPLING REACTIONS; ALUMINUM CHLORIDE; ACETYLENIC ESTERS; CONVENIENT ROUTE;

D O I：

10.1039/d0cy01379j

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The copper-catalyzed hydroboration of selenoalkynes in a regio- and stereoselective fashion is reported, delivering selenium-containing vinylboronate products in good yields. The reported protocol fills an important gap in the literature with respect to the synthesis of a valuable class of compounds, which is difficult to obtain otherwise.

引用

页码：7476 / 7480

页数：5

共 88 条

[51] Phosphine-Catalyzed Anti-Hydroboration of Internal Alkynes [J].

Nagao, Kazunori ;

Yamazaki, Ayaka ;

Ohmiya, Hirohisa ;

Sawamura, Masaya .

ORGANIC LETTERS, 2018, 20 (07) :1861-1865

[52] Benzoxaborole compounds for therapeutic uses: a patent review (2010-2018) [J].

Nocentini, Alessio ;

Supuran, Claudiu T. ;

Winum, Jean-Yves .

EXPERT OPINION ON THERAPEUTIC PATENTS, 2018, 28 (06) :493-504

[53] Organoselenium and organotellurium compounds: Toxicology and pharmacology [J].

Nogueira, CW ;

Zeni, G ;

Rocha, JBT .

CHEMICAL REVIEWS, 2004, 104 (12) :6255-6285

[54] Pd-Catalyzed Hydroborylation of Alkynes: A Ligand Controlled Regioselectivity Switch for the Synthesis of α- or β-Vinylboronates [J].

Ojha, Devi Prasan ;

Prabhu, Kandikere Ramaiah .

ORGANIC LETTERS, 2016, 18 (03) :432-435

[55] Regioselective Catalytic Hydroboration of Propargylic Species Using Cu(I)-NHC Complexes [J].

Park, Jin Kyoon ;

Ondrusek, Brian A. ;

McQuade, D. Tyler .

ORGANIC LETTERS, 2012, 14 (18) :4790-4793

[56] Copper(II)-Catalyzed -Borylation of Acetylenic Esters in Water [J].

Peck, Cheryl L. ;

Calderone, Joseph A. ;

Santos, Webster L. .

SYNTHESIS-STUTTGART, 2015, 47 (15) :2242-2248

[57] HYDROBORATION OF ALKYNES WITH PINACOLBORANE CATALYZED BY HZRCP(2)CL [J].

PEREIRA, S ;

SREBNIK, M .

ORGANOMETALLICS, 1995, 14 (07) :3127-3128

[58] A study of hydroboration of alkenes and alkynes with pinacolborane catalyzed by transition metals [J].

Pereira, S ;

Srebnik, M .

TETRAHEDRON LETTERS, 1996, 37 (19) :3283-3286

[59] Synthesis of Vinyl Selenides [J].

Perin, Gelson ;

Lenardao, Eder Joao ;

Jacob, Raquel Guimaraes ;

Panatieri, Rodrigo Barroso .

CHEMICAL REVIEWS, 2009, 109 (03) :1277-1301

[60]

Ponthieux S, 2000, TOP CURR CHEM, V208, P113

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