Linear and Angular Heteroacenes from Double-Electrophilic Cyclization (DEC) and DEC-Reductive Elimination of Diynes

Akhil Gupta; Bernard L. Flynn

doi:10.1021/acs.orglett.7b00265

Linear and Angular Heteroacenes from Double-Electrophilic Cyclization (DEC) and DEC-Reductive Elimination of Diynes

Akhil Gupta, Bernard L. Flynn

Medicinal Chemistry

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

30 Citations (Scopus)

Abstract

Linear and angular heteroacenes are prepared from terminal alkynes bearing tethered nucleophiles in two steps. Linear heteroacenes are formed from the homocoupling of these alkynes followed by reaction with a double electrophile (ECl₂) to induce a tricyclization reaction cascade involving double-electrophilic cyclization (DEC). Related angular heteroacenes are formed from the prior substitution of the chloro groups in ECl₂ with the same terminal alkyne followed by reaction with AuCl₃ to produce a DEC-reductive-elimination (DECRE) reaction.

Original language	English
Pages (from-to)	1939-1941
Number of pages	3
Journal	Organic Letters
Volume	19
Issue number	8
DOIs	https://doi.org/10.1021/acs.orglett.7b00265
Publication status	Published - 21 Apr 2017

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10.1021/acs.orglett.7b00265

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abstract = "Linear and angular heteroacenes are prepared from terminal alkynes bearing tethered nucleophiles in two steps. Linear heteroacenes are formed from the homocoupling of these alkynes followed by reaction with a double electrophile (ECl2) to induce a tricyclization reaction cascade involving double-electrophilic cyclization (DEC). Related angular heteroacenes are formed from the prior substitution of the chloro groups in ECl2 with the same terminal alkyne followed by reaction with AuCl3 to produce a DEC-reductive-elimination (DECRE) reaction.",

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N2 - Linear and angular heteroacenes are prepared from terminal alkynes bearing tethered nucleophiles in two steps. Linear heteroacenes are formed from the homocoupling of these alkynes followed by reaction with a double electrophile (ECl2) to induce a tricyclization reaction cascade involving double-electrophilic cyclization (DEC). Related angular heteroacenes are formed from the prior substitution of the chloro groups in ECl2 with the same terminal alkyne followed by reaction with AuCl3 to produce a DEC-reductive-elimination (DECRE) reaction.

AB - Linear and angular heteroacenes are prepared from terminal alkynes bearing tethered nucleophiles in two steps. Linear heteroacenes are formed from the homocoupling of these alkynes followed by reaction with a double electrophile (ECl2) to induce a tricyclization reaction cascade involving double-electrophilic cyclization (DEC). Related angular heteroacenes are formed from the prior substitution of the chloro groups in ECl2 with the same terminal alkyne followed by reaction with AuCl3 to produce a DEC-reductive-elimination (DECRE) reaction.

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Linear and Angular Heteroacenes from Double-Electrophilic Cyclization (DEC) and DEC-Reductive Elimination of Diynes

Abstract

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Chiral Catalysts by Rational Design

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Linear and Angular Heteroacenes from Double-Electrophilic Cyclization (DEC) and DEC-Reductive Elimination of Diynes

Abstract

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Chiral Catalysts by Rational Design

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