Hidden Boron Catalysis: Nucleophile-Promoted Decomposition of HBpin

被引：120

作者：

Bage, Andrew D. ^{[1
]}

Hunt, Thomas A. ^{[2
]}

Thomas, Stephen P. ^{[1
]}

机构：

[1] Univ Edinburgh, EaStCHEM Sch Chem, Edinburgh EH9 3FJ, Midlothian, Scotland

[2] AstraZeneca, Med Chem, Early Oncol, Cambridge CB4 0WG, England

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 11期

基金：

英国工程与自然科学研究理事会;

关键词：

SELECTIVE HYDROBORATION; ALDEHYDES; ALKENES; CATECHOLBORANE; KETONES; SPECTROSCOPY; DERIVATIVES; ALUMINUM; IMINES; ESTERS;

D O I：

10.1021/acs.orglett.0c01168

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Simple nucleophiles with structural similarities to known hydroboration catalysts can readily mediate the formation of BH3 and borohydride species from pinacolborane (HBpin). Alkyne and alkene hydroboration reactions were successfully mediated by nucleophiles through BH3 generation, with BH3-catalyzed hydroboration found to dominate catalysis. NMR spectroscopy and kinetic analyses showed that the nucleophiles (NaOBu)-Bu-t, Na[N(SiMe3)(2)], (Bu2Mg)-Bu-n, and (BuLi)-Bu-n only promoted the formation of BH3 and were not "true" hydroboration catalysts.

引用

页码：4107 / 4112

页数：6

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