Acid Promoted Tetrafunctionalization of Terminal Alkynes: Geminal Diazidation and Dibromination DOI

Zhiwu Fan,

Zhiqi Li,

Bao‐Yin Zhao

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(18), P. 3878 - 3882

Published: April 28, 2024

The synthesis of complex alkanes by the tetrafunctionalization alkynes is limited and challenging. Herein, an unprecedented efficient geminal diazidation dibromination terminal developed, which provides novel access to structurally diverse organic azides. approach has exclusive chemo- regioselectivity features mild reaction conditions, good tolerance various functional groups, more crucially, no metal involved in reaction, thereby benefiting late-stage decoration medicinal molecules. A mechanistic study showed that current proceeds via a radical pathway.

Language: Английский

Thiocyanate promoted difunctionalization and cyclization of unsaturated C–C bonds to construct 1-sulfur-2-nitrogen-functionalized alkenes and 2-thiocyanate indolines DOI

Hong Qin,

Feng Chen, Jinze Du

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(6), P. 1213 - 1218

Published: Jan. 1, 2024

An unprecedented one-pot route to achieve highly regioselective 1-sulfur-functionalized 2-nitrogen-functionalized alkenes and 2-thiocyanate indolines from unsymmetrical ynamides (readily generally available amides) using the commercially inexpensive iodobenzene diacetate (PIDA) as oxidant potassium thiocyanate (KSCN) (SCN) source has been developed. The interconversion of isothiocyanate (NCS) groups simultaneously forms C-N C-S bonds in this metal-free approach, while introducing important functional into homemade alkynes. A radical-chain mechanism, involving competing kinetically controlled chain transfer at S atom sterically-controlled N thiocyanogen molecule mild is proposed.

Language: Английский

Citations

0
Rhodium and Isothiourea Dual Catalysis: Enantiodivergent Transformation of Terminal Alkynes DOI

Tao Fan,

Zhipeng Shi,

Qian-Wei Gong

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(7), P. 1421 - 1425

Published: Feb. 12, 2024

A dual rhodium/isothiourea catalytic system was developed for the enantiodivergent transformation of terminal alkynes. Under synergistic catalysis, alkynes can be creatively utilized as precursors C1-ammonium enolate species, which subsequently participate in [4 + 2] and [2 annulation reactions with α,β-unsaturated ketimines or ketones, respectively. wide range chiral lactams lactones were obtained excellent yields stereoselectivities (up to >20:1 dr, 98% ee).

Language: Английский

Citations

0
Acid Promoted Tetrafunctionalization of Terminal Alkynes: Geminal Diazidation and Dibromination DOI

Zhiwu Fan,

Zhiqi Li,

Bao‐Yin Zhao

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(18), P. 3878 - 3882

Published: April 28, 2024

The synthesis of complex alkanes by the tetrafunctionalization alkynes is limited and challenging. Herein, an unprecedented efficient geminal diazidation dibromination terminal developed, which provides novel access to structurally diverse organic azides. approach has exclusive chemo- regioselectivity features mild reaction conditions, good tolerance various functional groups, more crucially, no metal involved in reaction, thereby benefiting late-stage decoration medicinal molecules. A mechanistic study showed that current proceeds via a radical pathway.

Language: Английский

Citations

0