Cupraelectro-Catalyzed Alkyne Annulation: Evidence for Distinct C-H Alkynylation and Decarboxylative C-H/C-C Manifolds

Cong Tian; Uttam Dhawa; Alexej Scheremetjew; Lutz Ackermann

doi:10.1021/acscatal.9b02348

Cupraelectro-Catalyzed Alkyne Annulation: Evidence for Distinct C-H Alkynylation and Decarboxylative C-H/C-C Manifolds

Cong Tian
, Uttam Dhawa
, Alexej Scheremetjew
, Lutz Ackermann^*

^*Corresponding author for this work

University of Göttingen

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

100 Citations (Scopus)

Abstract

Synthetically meaningful isoindolones were accessed by cupraelectro-catalyzed C-H activation with electricity as terminal oxidant. Thus, a versatile, inexpensive, and nontoxic Cu(OAc)₂ catalyst enabled broadly applicable C-H/N-H functionalizations on electron-rich and electron-deficient benzamides with distinct functional group tolerance and resource-economy. Detailed mechanistic studies provided strong support for a C-H alkynylation mechanism through fast C-H metalation, which likewise set the stage for cupraelectro-catalyzed C-H/C-C functionalizations in a decarboxylative fashion.

Original language	English
Pages (from-to)	7690-7696
Number of pages	7
Journal	ACS Catalysis
Volume	9
Issue number	9
DOIs	https://doi.org/10.1021/acscatal.9b02348
Publication status	Published - 6 Sept 2019
Externally published	Yes

Keywords

alkynylation
annulation
C-C cleavage
C-H activation
copper
electrochemistry
isoindolone

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10.1021/acscatal.9b02348

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title = "Cupraelectro-Catalyzed Alkyne Annulation: Evidence for Distinct C-H Alkynylation and Decarboxylative C-H/C-C Manifolds",

abstract = "Synthetically meaningful isoindolones were accessed by cupraelectro-catalyzed C-H activation with electricity as terminal oxidant. Thus, a versatile, inexpensive, and nontoxic Cu(OAc)2 catalyst enabled broadly applicable C-H/N-H functionalizations on electron-rich and electron-deficient benzamides with distinct functional group tolerance and resource-economy. Detailed mechanistic studies provided strong support for a C-H alkynylation mechanism through fast C-H metalation, which likewise set the stage for cupraelectro-catalyzed C-H/C-C functionalizations in a decarboxylative fashion.",

keywords = "alkynylation, annulation, C-C cleavage, C-H activation, copper, electrochemistry, isoindolone",

author = "Cong Tian and Uttam Dhawa and Alexej Scheremetjew and Lutz Ackermann",

note = "Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

year = "2019",

month = sep,

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doi = "10.1021/acscatal.9b02348",

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TY - JOUR

T1 - Cupraelectro-Catalyzed Alkyne Annulation

T2 - Evidence for Distinct C-H Alkynylation and Decarboxylative C-H/C-C Manifolds

AU - Tian, Cong

AU - Dhawa, Uttam

AU - Scheremetjew, Alexej

AU - Ackermann, Lutz

PY - 2019/9/6

Y1 - 2019/9/6

N2 - Synthetically meaningful isoindolones were accessed by cupraelectro-catalyzed C-H activation with electricity as terminal oxidant. Thus, a versatile, inexpensive, and nontoxic Cu(OAc)2 catalyst enabled broadly applicable C-H/N-H functionalizations on electron-rich and electron-deficient benzamides with distinct functional group tolerance and resource-economy. Detailed mechanistic studies provided strong support for a C-H alkynylation mechanism through fast C-H metalation, which likewise set the stage for cupraelectro-catalyzed C-H/C-C functionalizations in a decarboxylative fashion.

AB - Synthetically meaningful isoindolones were accessed by cupraelectro-catalyzed C-H activation with electricity as terminal oxidant. Thus, a versatile, inexpensive, and nontoxic Cu(OAc)2 catalyst enabled broadly applicable C-H/N-H functionalizations on electron-rich and electron-deficient benzamides with distinct functional group tolerance and resource-economy. Detailed mechanistic studies provided strong support for a C-H alkynylation mechanism through fast C-H metalation, which likewise set the stage for cupraelectro-catalyzed C-H/C-C functionalizations in a decarboxylative fashion.

KW - alkynylation

KW - annulation

KW - C-C cleavage

KW - C-H activation

KW - copper

KW - electrochemistry

KW - isoindolone

UR - https://www.scopus.com/pages/publications/85070599118

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DO - 10.1021/acscatal.9b02348

M3 - Article

AN - SCOPUS:85070599118

SN - 2155-5435

VL - 9

SP - 7690

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JO - ACS Catalysis

JF - ACS Catalysis

IS - 9

ER -

Cupraelectro-Catalyzed Alkyne Annulation: Evidence for Distinct C-H Alkynylation and Decarboxylative C-H/C-C Manifolds

Abstract

Keywords

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