Silver-Free Palladium-Catalyzed sp3 and sp2 C-H Alkynylation Promoted by a 1,2,3-Triazole Amine Directing Group

Xiaohan Ye; Chang Xu; Lukasz Wojtas; Novruz G. Akhmedov; Hao Chen; Xiaodong Shi

doi:10.1021/acs.orglett.6b01319

Silver-Free Palladium-Catalyzed sp³ and sp² C-H Alkynylation Promoted by a 1,2,3-Triazole Amine Directing Group

Xiaohan Ye, Chang Xu, Lukasz Wojtas, Novruz G. Akhmedov, Hao Chen, Xiaodong Shi

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

75 Scopus citations

Abstract

Triazole amine was identified as an effective directing group in promoting C-H alkynylation under silver-free conditions. No other external oxidant was required, and the alkynylation products were received in good to excellent yields. X-ray crystallographic analysis confirmed a direct C-H activation intermediate. Other typical directing groups, including pyridine amine (PIP) and 8-aminoquinoline (QA), gave almost no reaction under identical conditions, which highlighted the unique reactivity of the triazole directing group in direct C-H functionalization.

Original language	English (US)
Pages (from-to)	2970-2973
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	12
DOIs	https://doi.org/10.1021/acs.orglett.6b01319
State	Published - Jun 17 2016
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Silver-Free Palladium-Catalyzed sp3 and sp2 C-H Alkynylation Promoted by a 1,2,3-Triazole Amine Directing Group",

abstract = "Triazole amine was identified as an effective directing group in promoting C-H alkynylation under silver-free conditions. No other external oxidant was required, and the alkynylation products were received in good to excellent yields. X-ray crystallographic analysis confirmed a direct C-H activation intermediate. Other typical directing groups, including pyridine amine (PIP) and 8-aminoquinoline (QA), gave almost no reaction under identical conditions, which highlighted the unique reactivity of the triazole directing group in direct C-H functionalization.",

author = "Xiaohan Ye and Chang Xu and Lukasz Wojtas and Akhmedov, {Novruz G.} and Hao Chen and Xiaodong Shi",

note = "Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

year = "2016",

month = jun,

day = "17",

doi = "10.1021/acs.orglett.6b01319",

language = "English (US)",

volume = "18",

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journal = "Organic Letters",

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T1 - Silver-Free Palladium-Catalyzed sp3 and sp2 C-H Alkynylation Promoted by a 1,2,3-Triazole Amine Directing Group

AU - Ye, Xiaohan

AU - Xu, Chang

AU - Wojtas, Lukasz

AU - Akhmedov, Novruz G.

AU - Chen, Hao

AU - Shi, Xiaodong

PY - 2016/6/17

Y1 - 2016/6/17

N2 - Triazole amine was identified as an effective directing group in promoting C-H alkynylation under silver-free conditions. No other external oxidant was required, and the alkynylation products were received in good to excellent yields. X-ray crystallographic analysis confirmed a direct C-H activation intermediate. Other typical directing groups, including pyridine amine (PIP) and 8-aminoquinoline (QA), gave almost no reaction under identical conditions, which highlighted the unique reactivity of the triazole directing group in direct C-H functionalization.

AB - Triazole amine was identified as an effective directing group in promoting C-H alkynylation under silver-free conditions. No other external oxidant was required, and the alkynylation products were received in good to excellent yields. X-ray crystallographic analysis confirmed a direct C-H activation intermediate. Other typical directing groups, including pyridine amine (PIP) and 8-aminoquinoline (QA), gave almost no reaction under identical conditions, which highlighted the unique reactivity of the triazole directing group in direct C-H functionalization.

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JO - Organic Letters

JF - Organic Letters

IS - 12

ER -

Silver-Free Palladium-Catalyzed sp³ and sp² C-H Alkynylation Promoted by a 1,2,3-Triazole Amine Directing Group

Abstract

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