NHC-copper-thiophene-2-carboxylate complex for the hydroboration of terminal alkynes

Won Jun Jang; Byung Nam Kang; Ji Hun Lee; Yoon Mi Choi; Chong Hyeak Kim; Jaesook Yun

doi:10.1039/c9ob00839j

NHC-copper-thiophene-2-carboxylate complex for the hydroboration of terminal alkynes

Won Jun Jang
, Byung Nam Kang
, Ji Hun Lee
, Yoon Mi Choi
, Chong Hyeak Kim
, Jaesook Yun

Department of Chemistry & Nanoscience

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

18 Scopus citations

Abstract

An air-stable N-heterocyclic carbene-copper thiophene-2-carboxylate (CuTC) complex has been prepared for the stereoselective hydroboration of terminal alkynes using pinacolborane (HBpin) or 1,8-naphthalenediaminatoborane (HBdan). The newly synthesized complex can be directly activated by hydroboranes without a cocatalyst such as a base, and exhibits high reactivity for the hydroboration of alkynes under mild conditions. A gram-scale hydroboration of terminal phenylacetylene demonstrated the applicability of the copper complex for the preparation of alkenyl boronates.

Original language	English
Pages (from-to)	5249-5252
Number of pages	4
Journal	Organic and Biomolecular Chemistry
Volume	17
Issue number	21
DOIs	https://doi.org/10.1039/c9ob00839j
State	Published - 2019

Bibliographical note

Funding Information:
This study was supported by National Research Foundation of Korea (NRF) grants (No. 2016R1A2B4011719 and 2019R1A2C2005706), funded by the Korean government (MEST).

Publisher Copyright:
© 2019 The Royal Society of Chemistry.

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10.1039/c9ob00839j

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title = "NHC-copper-thiophene-2-carboxylate complex for the hydroboration of terminal alkynes",

abstract = "An air-stable N-heterocyclic carbene-copper thiophene-2-carboxylate (CuTC) complex has been prepared for the stereoselective hydroboration of terminal alkynes using pinacolborane (HBpin) or 1,8-naphthalenediaminatoborane (HBdan). The newly synthesized complex can be directly activated by hydroboranes without a cocatalyst such as a base, and exhibits high reactivity for the hydroboration of alkynes under mild conditions. A gram-scale hydroboration of terminal phenylacetylene demonstrated the applicability of the copper complex for the preparation of alkenyl boronates.",

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note = "Funding Information: This study was supported by National Research Foundation of Korea (NRF) grants (No. 2016R1A2B4011719 and 2019R1A2C2005706), funded by the Korean government (MEST). Publisher Copyright: {\textcopyright} 2019 The Royal Society of Chemistry.",

year = "2019",

doi = "10.1039/c9ob00839j",

language = "English",

volume = "17",

pages = "5249--5252",

journal = "Organic and Biomolecular Chemistry",

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T1 - NHC-copper-thiophene-2-carboxylate complex for the hydroboration of terminal alkynes

AU - Jang, Won Jun

AU - Kang, Byung Nam

AU - Lee, Ji Hun

AU - Choi, Yoon Mi

AU - Kim, Chong Hyeak

AU - Yun, Jaesook

N1 - Funding Information: This study was supported by National Research Foundation of Korea (NRF) grants (No. 2016R1A2B4011719 and 2019R1A2C2005706), funded by the Korean government (MEST). Publisher Copyright: © 2019 The Royal Society of Chemistry.

PY - 2019

Y1 - 2019

N2 - An air-stable N-heterocyclic carbene-copper thiophene-2-carboxylate (CuTC) complex has been prepared for the stereoselective hydroboration of terminal alkynes using pinacolborane (HBpin) or 1,8-naphthalenediaminatoborane (HBdan). The newly synthesized complex can be directly activated by hydroboranes without a cocatalyst such as a base, and exhibits high reactivity for the hydroboration of alkynes under mild conditions. A gram-scale hydroboration of terminal phenylacetylene demonstrated the applicability of the copper complex for the preparation of alkenyl boronates.

AB - An air-stable N-heterocyclic carbene-copper thiophene-2-carboxylate (CuTC) complex has been prepared for the stereoselective hydroboration of terminal alkynes using pinacolborane (HBpin) or 1,8-naphthalenediaminatoborane (HBdan). The newly synthesized complex can be directly activated by hydroboranes without a cocatalyst such as a base, and exhibits high reactivity for the hydroboration of alkynes under mild conditions. A gram-scale hydroboration of terminal phenylacetylene demonstrated the applicability of the copper complex for the preparation of alkenyl boronates.

UR - https://www.scopus.com/pages/publications/85066436452

U2 - 10.1039/c9ob00839j

DO - 10.1039/c9ob00839j

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AN - SCOPUS:85066436452

SN - 1477-0520

VL - 17

SP - 5249

EP - 5252

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 21

ER -

NHC-copper-thiophene-2-carboxylate complex for the hydroboration of terminal alkynes

Abstract

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