Stereo- and Regiocontrolled Methylboration of Terminal Alkynes

Oleksandr Zhurakovskyi; Rafael M.P. Dias; Adam Noble; Varinder K. Aggarwal

doi:10.1021/acs.orglett.8b01252

Stereo- and Regiocontrolled Methylboration of Terminal Alkynes

Oleksandr Zhurakovskyi, Rafael M.P. Dias, Adam Noble, Varinder K. Aggarwal^*

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

17 Citations (Scopus)

442 Downloads (Pure)

Abstract

A scalable and operationally simple synthesis of trisubstituted alkenyl boronic esters has been achieved using a Zr-catalyzed carboalumination of terminal alkynes followed by in situ transmetalation with i-PrOBpin. The products are formed in good yields and with excellent regioselectivity and perfect stereoselectivity. The new procedure provides a significant improvement over the previously reported syntheses.

Original language	English
Pages (from-to)	3136-3139
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	10
Early online date	9 May 2018
DOIs	https://doi.org/10.1021/acs.orglett.8b01252
Publication status	Published - 18 May 2018

Research Groups and Themes

Organic & Biological

Access to Document

10.1021/acs.orglett.8b01252

Full-text PDF (final published version)
This is the final published version of the article (version of record). It first appeared online via ACS at https://doi.org/10.1021/acs.orglett.8b01252 . Please refer to any applicable terms of use of the publisher.
Final published version, 959 KBLicence: CC BY
Supplementary information PDF
This is the final published version of the article (version of record). It first appeared online via ACS at https://doi.org/10.1021/acs.orglett.8b01252 . Please refer to any applicable terms of use of the publisher.
Final published version, 3.46 MBLicence: CC BY

Handle.net

Persistent link

Cite this

@article{cb79b7bcc0d649ae811f75b297e02761,

title = "Stereo- and Regiocontrolled Methylboration of Terminal Alkynes",

abstract = "A scalable and operationally simple synthesis of trisubstituted alkenyl boronic esters has been achieved using a Zr-catalyzed carboalumination of terminal alkynes followed by in situ transmetalation with i-PrOBpin. The products are formed in good yields and with excellent regioselectivity and perfect stereoselectivity. The new procedure provides a significant improvement over the previously reported syntheses.",

author = "Oleksandr Zhurakovskyi and Dias, \{Rafael M.P.\} and Adam Noble and Aggarwal, \{Varinder K.\}",

year = "2018",

month = may,

day = "18",

doi = "10.1021/acs.orglett.8b01252",

language = "English",

volume = "20",

pages = "3136--3139",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "10",

}

TY - JOUR

T1 - Stereo- and Regiocontrolled Methylboration of Terminal Alkynes

AU - Zhurakovskyi, Oleksandr

AU - Dias, Rafael M.P.

AU - Noble, Adam

AU - Aggarwal, Varinder K.

PY - 2018/5/18

Y1 - 2018/5/18

N2 - A scalable and operationally simple synthesis of trisubstituted alkenyl boronic esters has been achieved using a Zr-catalyzed carboalumination of terminal alkynes followed by in situ transmetalation with i-PrOBpin. The products are formed in good yields and with excellent regioselectivity and perfect stereoselectivity. The new procedure provides a significant improvement over the previously reported syntheses.

AB - A scalable and operationally simple synthesis of trisubstituted alkenyl boronic esters has been achieved using a Zr-catalyzed carboalumination of terminal alkynes followed by in situ transmetalation with i-PrOBpin. The products are formed in good yields and with excellent regioselectivity and perfect stereoselectivity. The new procedure provides a significant improvement over the previously reported syntheses.

UR - https://www.scopus.com/pages/publications/85047296491

U2 - 10.1021/acs.orglett.8b01252

DO - 10.1021/acs.orglett.8b01252

M3 - Article (Academic Journal)

C2 - 29741904

SN - 1523-7060

VL - 20

SP - 3136

EP - 3139

JO - Organic Letters

JF - Organic Letters

IS - 10

ER -

Stereo- and Regiocontrolled Methylboration of Terminal Alkynes

Abstract

Research Groups and Themes

Access to Document

Handle.net

Other files and links

Fingerprint

FRESCO: Efficient, Flexible Synthesis of Molecules with Tailored Shapes: from Photoswitchable Helices to anti-Cancer Compounds

Changing the Synthesis Landscape with Boron at the Helm: from Chiral Organometallics to Assembly Line Synthesis

Cite this

Stereo- and Regiocontrolled Methylboration of Terminal Alkynes

Abstract

Research Groups and Themes

Access to Document

Handle.net

Other files and links

Fingerprint

Projects

FRESCO: Efficient, Flexible Synthesis of Molecules with Tailored Shapes: from Photoswitchable Helices to anti-Cancer Compounds

Changing the Synthesis Landscape with Boron at the Helm: from Chiral Organometallics to Assembly Line Synthesis

Cite this