Reactions of Haloalkynes

Jiang, Huanfeng; Zhu, Chuanle; Wu, Wanqing

doi:10.1007/978-3-662-49001-3_3

Search citation statements

Order By: Relevance

Paper Sections

Select...

Direct Alkynylation With 1-haloalkynes or Gem-dihaloalkenes1

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2017

2021

Publication Types

Select...

Article2

Relationship

Self Cite0

Independent2

Authors

Journals

Cited by 2 publications

(1 citation statement)

References 241 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[40][41][42] Recently, the development of a complementary strategy, called "direct alkynylation" or even "inverse Sonogashira coupling", which involves the direct alkynylation of Csp2-H bonds of (hetero)arenes with alkynyl halides (Scheme 2) has gained much interest. [33,[43][44][45][46][47][48][49]…”

Section: Direct Alkynylation With 1-haloalkynes or Gem-dihaloalkenesmentioning

confidence: 99%

Undirected, Selective Csp2-H Alkynylation of Five-membered Heteroarenes

Bellina

Manna

Rosadoni

2021

COC

View full text Add to dashboard Cite

: The functionalization of Csp2-H bond of heteroarene with an alkyne represents one of the most attractive procedures for the late-stage functionalization of the aromatic core due to the structural characteristics and synthetic versatility given by a triple carbon-carbon bond. The aim of this review is to cover the most significant results reported in the literature regarding the synthesis of alkynyl-substituted five-membered heteroarenes by selective direct Csp2-H alkynylation with 1-haloalkynes and analogs, or by cross-dehydrogenative alkynylation (CDA) with terminal alkynes, without making use of directing groups.

show abstract

Section: Direct Alkynylation With 1-haloalkynes or Gem-dihaloalkenesmentioning

confidence: 99%

Undirected, Selective Csp2-H Alkynylation of Five-membered Heteroarenes

Bellina

Manna

Rosadoni

2021

COC

View full text Add to dashboard Cite

show abstract

Copper-Catalyzed Hydrogen/Iodine Exchange in Terminal and 1-Iodoalkynes

Chung

Hein

2017

ACS Catal.

View full text Add to dashboard Cite

Detailed kinetic profiles of the copper-catalyzed exchange between the acetylenic proton and iodide of terminal and 1-iodophenylacetylenes are reported. The electronic nature of the alkynes does not influence the equilibrium of the exchange (K eq = 1), only the rate of equilibration. Notably, the profiles are the same for electron-rich, methyl-substituted phenylacetylenes but are divergent for electron-deficient, trifluoromethyl-substituted variants. The heretofore unreported exchange process yields practical considerations regarding reactions involving iodo and terminal alkynes.

show abstract

Reactions of Haloalkynes

Cited by 2 publications

References 241 publications

Undirected, Selective Csp2-H Alkynylation of Five-membered Heteroarenes

Undirected, Selective Csp2-H Alkynylation of Five-membered Heteroarenes

Copper-Catalyzed Hydrogen/Iodine Exchange in Terminal and 1-Iodoalkynes

Contact Info

Product

Resources

About