Boryl-Directed, Ir-Catalyzed C(sp3)-H Borylation of Alkylboronic Acids Leading to Site-Selective Synthesis of Polyborylalkanes

被引：33

作者：

Yamamoto, Takeshi ^{[1
]}

Ishibashi, Aoi ^{[1
]}

Suginome, Michinori ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Engn, Dept Synthet Chem & Biol Chem, Nishikyo Ku, Kyoto 6158510, Japan

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 16期

关键词：

C-H BONDS; ALLYLIC SUBSTITUTION; ARYLBORONIC ACIDS; ALKYL-HALIDES; DIBORYLMETHANE; ESTERS; DIBORYLATION; 1,1-DIBORYLALKANES; FUNCTIONALIZATION; SCOPE;

D O I：

10.1021/acs.orglett.9b02112

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Pyrazolylaniline serves as a temporary directing group attached to the boron atom of alkylboronic acids in Ir-catalyzed C(sp(3))-H borylation. The reaction takes place at alpha-, beta-, and gamma-C-H bonds, giving polyborylated products including di-, tri-, tetra-, and even pentaborylalkanes. alpha-C-H borylation was generally found to be the preferred reaction of primary alkylboronic acid derivatives, whereas beta- or gamma-borylation also occurred if beta- or gamma-C-H bonds were located on the methyl group.

引用

页码：6235 / 6240

页数：6

共 87 条

[1] Addition reactions of bis(pinacolato)diborane(4) to carbonyl enones and synthesis of (pinacolato)2BCH2B and (pinacolato)2BCH2CH2B by insertion and coupling [J].