Simple access to elusive α-boryl carbanions and their alkylation: An umpolung construction for organic synthesis

Kai Hong; Xun Liu; James P. Morken

doi:10.1021/ja505455z

Simple access to elusive α-boryl carbanions and their alkylation: An umpolung construction for organic synthesis

Kai Hong
, Xun Liu
, James P. Morken^*

^*Corresponding author for this work

Boston College

Research output: Contribution to journal › Article › peer-review

257 Scopus citations

Abstract

The reaction of 1,1-bis(pinacolboronate) esters with alkyl halides can be effected by metal alkoxides and provides a strategy for the construction of organoboronate compounds. The reaction is found to occur by alkoxide-induced deborylation and generation of a boron-stabilized carbanion.

Original language	English
Pages (from-to)	10581-10584
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	136
Issue number	30
DOIs	https://doi.org/10.1021/ja505455z
State	Published - 30 Jul 2014
Externally published	Yes

Access to Document

10.1021/ja505455z

Cite this

@article{65bba90ccdbf407aa816d7fbd514a7ea,

title = "Simple access to elusive α-boryl carbanions and their alkylation: An umpolung construction for organic synthesis",

abstract = "The reaction of 1,1-bis(pinacolboronate) esters with alkyl halides can be effected by metal alkoxides and provides a strategy for the construction of organoboronate compounds. The reaction is found to occur by alkoxide-induced deborylation and generation of a boron-stabilized carbanion.",

author = "Kai Hong and Xun Liu and Morken, \{James P.\}",

year = "2014",

month = jul,

day = "30",

doi = "10.1021/ja505455z",

language = "英语",

volume = "136",

pages = "10581--10584",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "30",

}

TY - JOUR

T1 - Simple access to elusive α-boryl carbanions and their alkylation

T2 - An umpolung construction for organic synthesis

AU - Hong, Kai

AU - Liu, Xun

AU - Morken, James P.

PY - 2014/7/30

Y1 - 2014/7/30

N2 - The reaction of 1,1-bis(pinacolboronate) esters with alkyl halides can be effected by metal alkoxides and provides a strategy for the construction of organoboronate compounds. The reaction is found to occur by alkoxide-induced deborylation and generation of a boron-stabilized carbanion.

AB - The reaction of 1,1-bis(pinacolboronate) esters with alkyl halides can be effected by metal alkoxides and provides a strategy for the construction of organoboronate compounds. The reaction is found to occur by alkoxide-induced deborylation and generation of a boron-stabilized carbanion.

UR - https://www.scopus.com/pages/publications/84905277300

U2 - 10.1021/ja505455z

DO - 10.1021/ja505455z

M3 - 文章

C2 - 25019925

AN - SCOPUS:84905277300

SN - 0002-7863

VL - 136

SP - 10581

EP - 10584

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 30

ER -

Simple access to elusive α-boryl carbanions and their alkylation: An umpolung construction for organic synthesis

Abstract

Access to Document

Other files and links

Fingerprint

Cite this