Transition-Metal-Free Allylic Borylation of 1,3-Dienes

被引：22

作者：

Maza, Ricardo J. ^{[1
]}

Davenport, Elliot ^{[1
,2
]}

Miralles, Nuria ^{[1
]}

Carbo, Jorge J. ^{[1
]}

Fernandez, Elena ^{[1
]}

机构：

[1] Univ Rovira & Virgili, Dept Quim Fis & Inorgan, C Marcelli Domingo 1, Tarragona 43007, Spain

[2] Univ Edinburgh, Dept Chem, Edinburgh EH9 3FJ, Midlothian, Scotland

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 07期

关键词：

CATALYZED 1,4-HYDROBORATION; CONJUGATED DIENES; DIBORATION; 1,4-DIBORATION; HYDROBORATION; ALDEHYDES;

D O I：

10.1021/acs.orglett.9b00531

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This work explains the reactivity of diboron reagents with 1,3-dienes in a transition-metal-free context. The sole addition of Na2CO3 (30 mol %) to bis(pinacolato)diboron in MeOH allows the 1,4-hydroboration of cyclic and noncyclic 1,3-dienes. The electronic influence on the substrate guarantees the conjugated 1,4-hydroboration versus 1,2-diboration. DFT calculations show that the distribution of charge in the allylic anion intermediate governs the selectivity toward 1,4-hydroboration, while the favored trans configuration in diene reagents determines the preference for the E allyl boronate products.

引用

页码：2251 / 2255

页数：5

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