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

Akhil Gupta, Bernard L. Flynn

Research output: Contribution to journalArticleResearchpeer-review

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 languageEnglish
Pages (from-to)1939-1941
Number of pages3
JournalOrganic Letters
Volume19
Issue number8
DOIs
Publication statusPublished - 21 Apr 2017

Cite this

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title = "Linear and Angular Heteroacenes from Double-Electrophilic Cyclization (DEC) and DEC-Reductive Elimination of Diynes",
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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journal = "Organic Letters",
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Linear and Angular Heteroacenes from Double-Electrophilic Cyclization (DEC) and DEC-Reductive Elimination of Diynes. / Gupta, Akhil; Flynn, Bernard L.

In: Organic Letters, Vol. 19, No. 8, 21.04.2017, p. 1939-1941.

Research output: Contribution to journalArticleResearchpeer-review

TY - JOUR

T1 - Linear and Angular Heteroacenes from Double-Electrophilic Cyclization (DEC) and DEC-Reductive Elimination of Diynes

AU - Gupta, Akhil

AU - Flynn, Bernard L.

PY - 2017/4/21

Y1 - 2017/4/21

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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U2 - 10.1021/acs.orglett.7b00265

DO - 10.1021/acs.orglett.7b00265

M3 - Article

VL - 19

SP - 1939

EP - 1941

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 8

ER -