scholarly journals Copper-catalyzed direct transformation of simple alkynes to alkenyl nitriles via aerobic oxidative N-incorporation

2015 ◽  
Vol 6 (11) ◽  
pp. 6355-6360 ◽  
Author(s):  
Xiaoqiang Huang ◽  
Xinyao Li ◽  
Ning Jiao
Keyword(s):  
Late Stage ◽  
Copper Catalyst ◽  
Terminal Alkynes ◽  
Direct Transformation ◽  
N Incorporation

A novel Cu-catalyzed aerobic oxidative N-incorporation into aliphatic terminal alkynes for the synthesis of alkenyl nitriles has been reported. The usage of inexpensive copper catalyst, O2as the sole oxidant, broad substrate scope as well as the feasibility for “the late-stage modification” make this protocol very promising.

Efficient Carboxylation of Terminal Alkynes with Carbon Dioxide Catalyzed by Ligand‐Free Copper Catalyst under Ambient Conditions

2019 ◽  
Vol 8 (8) ◽  
pp. 1501-1505 ◽  
Author(s):  
Wan‐Hui Wang ◽  
Lihong Jia ◽  
Xiujuan Feng ◽  
Dingqiao Fang ◽  
Hongyu Guo ◽  
...  
Keyword(s):  
Carbon Dioxide ◽  
Copper Catalyst ◽  
Terminal Alkynes ◽  
Ambient Conditions ◽  
Ligand Free

scholarly journals One-Pot Synthesis of (Z)-β-Halovinyl Ketones via the Cascade of Sonogashira Coupling and Hydrohalogenation

2021 ◽  
Vol 8 ◽  
Author(s):  
Fa-Jie Chen ◽  
Zhenguo Hua ◽  
Jianhui Chen ◽  
Jiajia Chen ◽  
Daesung Lee ◽  
...  
Keyword(s):  
Efficient Method ◽  
Room Temperature ◽  
Copper Catalyst ◽  
High Yield ◽  
Sonogashira Coupling ◽  
Terminal Alkynes ◽  
Acid Chlorides ◽  
Triflic Acid ◽  
One Pot

Herein, we report an efficient method for the synthesis of (Z)-β-halovinyl ketones through a one-pot Sonogashira coupling and hydrohalogenation reaction promoted by palladium-copper catalyst and Brønsted acid. The ynone intermediates are generated in situ from readily available acid chlorides and terminal alkynes at room temperature, which are directly converted to (Z)-β-halovinyl ketones by treating with triflic acid. This method avoids the use of an external halogen source and features broad substrate scope, high yield, and good to excellent stereoselectivity.

scholarly journals Co-Catalyzed E-(β)-Selective Hydrogermylation of Terminal Alkynes

2021 ◽  
Author(s):  
Maxim Radzhabov ◽  
Neal Mankad
Keyword(s):  
Natural Products ◽  
Late Stage ◽  
Functional Group ◽  
Terminal Alkynes ◽  
Mechanistic Studies ◽  
Practical Utility ◽  
Π Complex ◽  
Accessible Method ◽  
High Yields

<a></a><a>We demonstrated unprecedentedly that Co complexes can catalyze hydrogermylation of alkynes. Subsequently, a selective, accessible method was developed to synthesize E-(β)-vinyl(trialkyl)germanes from various terminal alkynes with high yields. As shown on multiple examples, the developed method demonstrates broad functional group tolerance and practical utility for late-stage hydrogermylation of drugs and natural products. The method is compatible with alkynes bearing both aryl and alkyl substituents, providing unrivaled selectivity for previously challenging 1° alkyl-substituted alkynes. Moreover, the catalyst used in this method, Co<sub>2</sub>(CO)<sub>8</sub>, is a cheap and commercially available reagent. Conducted mechanistic studies supported syn-addition of Bu<sub>3</sub>GeH to an alkyne</a> π-complex.

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

2021 ◽  
Vol 25 ◽  
Author(s):  
Fabio Bellina ◽  
Martina La Manna ◽  
Elisabetta Rosadoni
Keyword(s):  
Late Stage ◽  
Structural Characteristics ◽  
Terminal Alkynes ◽  
Carbon Bond ◽  
Carbon Carbon Bond

: 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.

scholarly journals Co-Catalyzed E-(β)-Selective Hydrogermylation of Terminal Alkynes

2021 ◽  
Author(s):  
Maxim Radzhabov ◽  
Neal Mankad
Keyword(s):  
Natural Products ◽  
Late Stage ◽  
Functional Group ◽  
Terminal Alkynes ◽  
Mechanistic Studies ◽  
Practical Utility ◽  
Π Complex ◽  
Accessible Method ◽  
High Yields

<a></a><a>We demonstrated unprecedentedly that Co complexes can catalyze hydrogermylation of alkynes. Subsequently, a selective, accessible method was developed to synthesize E-(β)-vinyl(trialkyl)germanes from various terminal alkynes with high yields. As shown on multiple examples, the developed method demonstrates broad functional group tolerance and practical utility for late-stage hydrogermylation of drugs and natural products. The method is compatible with alkynes bearing both aryl and alkyl substituents, providing unrivaled selectivity for previously challenging 1° alkyl-substituted alkynes. Moreover, the catalyst used in this method, Co<sub>2</sub>(CO)<sub>8</sub>, is a cheap and commercially available reagent. Conducted mechanistic studies supported syn-addition of Bu<sub>3</sub>GeH to an alkyne</a> π-complex.

Cobalt-catalyzed Glaser-type Homocoupling Reaction

Synthesis ◽  
2021 ◽  
Author(s):  
Keyin Ye ◽  
Jun-Fa Han ◽  
Peng Guo ◽  
Lin Chen
Keyword(s):  
Natural Products ◽  
Late Stage ◽  
Terminal Alkynes ◽  
Reaction Conditions ◽  
Highly Efficient ◽  
Homocoupling Reaction

A highly efficient cobalt-catalyzed homocoupling of terminal alkynes with di-tert-butyldiaziridinone as the oxidant has been developed. The protocol tolerates a wide array of terminal alkynes, both activated and unactivated alkynes, to afford their corresponding conjugated 1,3-diynes. The mild reaction conditions further allow late-stage homocoupling of alkynes derived from complex natural products.

General and selective syn-carboxylation-trifluoromethylation of terminal alkynes: application to the late-stage modification of dehydrocholic acid

2019 ◽  
Vol 55 (28) ◽  
pp. 4099-4102 ◽  
Author(s):  
Song-Lin Zhang ◽  
Chang Xiao ◽  
Hai-Xing Wan ◽  
Xiaoming Zhang
Keyword(s):  
Late Stage ◽  
Triple Bond ◽  
Biologically Active ◽  
Terminal Alkynes ◽  
Dehydrocholic Acid ◽  
Enol Esters

A general and selective syn-carboxylation-trifluoromethylation across the triple bond of terminal alkynes is developed by virtue of a reactive Cu(iii)–CF3 complex, which produces a broad range of biologically active trifluoromethylated enol esters with excellent regio- and stereoselectivity.

scholarly journals Enantiocontrol by assembled attractive interactions in copper-catalyzed asymmetric direct alkynylation of α-ketoesters with terminal alkynes: OH⋯O/sp3-CH⋯O two-point hydrogen bonding combined with dispersive attractions

2018 ◽  
Vol 9 (14) ◽  
pp. 3484-3493 ◽  
Author(s):  
Martin C. Schwarzer ◽  
Akane Fujioka ◽  
Takaoki Ishii ◽  
Hirohisa Ohmiya ◽  
Seiji Mori ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Copper Catalyst ◽  
Terminal Alkynes

A chiral copper catalyst selects enantiofaces by assembled attractive interactions.

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