Visible-Light-Induced In Situ Generation of Fischer-Type Copper Carbene Complexes from Acylsilanes and Its Application to Catalytic [4+1] Cycloaddition with Siloxydienes

被引：37

作者：

Takeuchi, Taiichi ^{[1
]}

Aoyama, Tsukasa ^{[1
]}

Orihara, Kurumi ^{[1
]}

Ishida, Kento ^{[1
]}

Kusama, Hiroyuki ^{[1
]}

机构：

[1] Gakushuin Univ, Fac Sci, Dept Chem, Tokyo 1718588, Japan

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 24期

关键词：

LATE TRANSITION-METALS; MECHANISTIC PHOTOCHEMISTRY; REGIOSELECTIVE SYNTHESIS; SELF-DIMERIZATION; 3+2 CYCLIZATION; TRANSMETALATION; DERIVATIVES; BENZOYLTRIMETHYLSILANE; SILYLACYLATIONS; SILOXYCARBENES;

D O I：

10.1021/acs.orglett.1c03683

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel methodology for in situ generation of Fischer-type metal-carbene complexes was developed. Photoirradiation to a mixture of an acylsilane and a cationic copper complex cleanly gave a Fischer-type copper-siloxycarbene complex, which was detected by spectroscopic methods. This carbene complex reacted with siloxydienes in a [4 + 1] cycloaddition manner to give cyclopentene derivatives. It is noteworthy that this reaction proceeds with a catalytic amount of copper through in situ generation of a Fischer-type copper-siloxycarbene complex intermediate.

引用

页码：9490 / 9494

页数：5

共 66 条

[1]

Albéniz AC, 2002, ANGEW CHEM INT EDIT, V41, P2363, DOI 10.1002/1521-3773(20020703)41:13<2363::AID-ANIE2363>3.0.CO

[2]

2-9

[3] Regioselective Synthesis of α,α-Difluorocyclopentanone Derivatives: Domino Nickel-Catalyzed Difluorocyclopropanation/Ring-Expansion Sequence of Silyl Dienol Ethers [J].

Aono, Tatsuya ;

Sasagawa, Hisashi ;

Fuchibe, Kohei ;

Ichikawa, Junji .

ORGANIC LETTERS, 2015, 17 (23) :5736-5739

[4] NEW GOLD CARBENE COMPLEXES VIA CARBENE TRANSFER-REACTIONS [J].

AUMANN, R ;

FISCHER, EO .

CHEMISCHE BERICHTE-RECUEIL, 1981, 114 (05) :1853-1857

[5] Metal-controlled selective [3+2] cyclization reactions of alkenyl Fischer carbene complexes and allenes [J].

Barluenga, J ;

Vicente, R ;

Barrio, P ;

López, LA ;

Tomás, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (19) :5974-5975

[6] New Fischer carbene complexes of rhodium(I):: Preparation and 2-cyclopentenone ring synthesis by annelation to alkynes [J].

Barluenga, J ;

Vicente, R ;

López, LA ;

Rubio, E ;

Tomás, M ;

Alvarez-Rúa, C .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (02) :470-471

[7]

Barluenga J, 2001, ANGEW CHEM INT EDIT, V40, P3392, DOI 10.1002/1521-3773(20010917)40:18<3392::AID-ANIE3392>3.0.CO

[8]

2-Y

[9] A general and regioselective synthesis of cyclopentenone derivatives through nickel(0)-mediated [3+2] cyclization of alkenyl Fischer carbene complexes and internal alkynes [J].

Barluenga, Jose ;

Barrio, Pablo ;

Riesgo, Lorena ;

Lopez, Luis. A. ;

Tomas, Miguel .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (46) :14422-14426

[10] Highly chemo-, regio-, and stereoselective [3+2]-cyclization of activated and deactivated allenes with alkenyl Fischer carbene complexes:: A straightforward access to alkylidenecyclopentanone derivatives [J].

Barluenga, Jose ;

Vicente, Ruben ;

Lopez, Luis A. ;

Tomas, Miguel .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) :7050-7054

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