Copper-Catalyzed Vicinal Cyano-, Thiocyano-, and Chlorophosphorylation of Alkynes: A Phosphinoyl Radical-Initiated Approach for Difunctionalized Alkenes

Ze Kun Tao; Cheng Kun Li; Jian An Li; Adedamola Shoberu; Wei Zhang; Jian Ping Zou

doi:10.1021/acs.orglett.1c01286

Copper-Catalyzed Vicinal Cyano-, Thiocyano-, and Chlorophosphorylation of Alkynes: A Phosphinoyl Radical-Initiated Approach for Difunctionalized Alkenes

Ze Kun Tao
, Cheng Kun Li
, Jian An Li
, Adedamola Shoberu
, Wei Zhang
, Jian Ping Zou

Chemistry

Soochow University

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

Abstract

A copper-catalyzed difunctional cyano-, thiocyano-, and chlorophosphorylation reaction of alkynes with P(O)-H compounds and coupling partners (TBACN, TMSNCS, TMSCl) is described. The reaction introduces versatile groups (-P(O)R2 and -CN, -SCN, or -Cl) to form tri- and tetrasubstituted alkenyl phosphine oxides/phosphonates regio- and stereoselectively.

Original language	English
Pages (from-to)	4342-4347
Number of pages	6
Journal	Organic Letters
Volume	23
Issue number	11
DOIs	https://doi.org/10.1021/acs.orglett.1c01286
State	Published - Jun 4 2021

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/acs.orglett.1c01286

Cite this

@article{d485b5302863439787c3bf0ddf8b4d5b,

title = "Copper-Catalyzed Vicinal Cyano-, Thiocyano-, and Chlorophosphorylation of Alkynes: A Phosphinoyl Radical-Initiated Approach for Difunctionalized Alkenes",

abstract = "A copper-catalyzed difunctional cyano-, thiocyano-, and chlorophosphorylation reaction of alkynes with P(O)-H compounds and coupling partners (TBACN, TMSNCS, TMSCl) is described. The reaction introduces versatile groups (-P(O)R2 and -CN, -SCN, or -Cl) to form tri- and tetrasubstituted alkenyl phosphine oxides/phosphonates regio- and stereoselectively.",

author = "Tao, \{Ze Kun\} and Li, \{Cheng Kun\} and Li, \{Jian An\} and Adedamola Shoberu and Wei Zhang and Zou, \{Jian Ping\}",

note = "Publisher Copyright: {\textcopyright} 2021 American Chemical Society.",

year = "2021",

month = jun,

day = "4",

doi = "10.1021/acs.orglett.1c01286",

language = "English",

volume = "23",

pages = "4342--4347",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "11",

}

TY - JOUR

T1 - Copper-Catalyzed Vicinal Cyano-, Thiocyano-, and Chlorophosphorylation of Alkynes

T2 - A Phosphinoyl Radical-Initiated Approach for Difunctionalized Alkenes

AU - Tao, Ze Kun

AU - Li, Cheng Kun

AU - Li, Jian An

AU - Shoberu, Adedamola

AU - Zhang, Wei

AU - Zou, Jian Ping

PY - 2021/6/4

Y1 - 2021/6/4

N2 - A copper-catalyzed difunctional cyano-, thiocyano-, and chlorophosphorylation reaction of alkynes with P(O)-H compounds and coupling partners (TBACN, TMSNCS, TMSCl) is described. The reaction introduces versatile groups (-P(O)R2 and -CN, -SCN, or -Cl) to form tri- and tetrasubstituted alkenyl phosphine oxides/phosphonates regio- and stereoselectively.

AB - A copper-catalyzed difunctional cyano-, thiocyano-, and chlorophosphorylation reaction of alkynes with P(O)-H compounds and coupling partners (TBACN, TMSNCS, TMSCl) is described. The reaction introduces versatile groups (-P(O)R2 and -CN, -SCN, or -Cl) to form tri- and tetrasubstituted alkenyl phosphine oxides/phosphonates regio- and stereoselectively.

UR - https://www.scopus.com/pages/publications/85107712449

UR - https://www.scopus.com/pages/publications/85107712449#tab=citedBy

U2 - 10.1021/acs.orglett.1c01286

DO - 10.1021/acs.orglett.1c01286

M3 - Article

C2 - 34029107

AN - SCOPUS:85107712449

SN - 1523-7060

VL - 23

SP - 4342

EP - 4347

JO - Organic Letters

JF - Organic Letters

IS - 11

ER -

Copper-Catalyzed Vicinal Cyano-, Thiocyano-, and Chlorophosphorylation of Alkynes: A Phosphinoyl Radical-Initiated Approach for Difunctionalized Alkenes

Abstract

ASJC Scopus Subject Areas

Access to Document

Other files and links

Fingerprint

Cite this