P. D. Forgione, A. G. Wilson, and . Fallis, Magnesium mediated carbometallation of propargyl alcohols: direct routes to furans and furanones, Tetrahedron Letters, vol.41, issue.1, p.17, 2000.
DOI : 10.1016/S0040-4039(99)01995-4

P. D. Forgione, G. P. Wilson, and A. G. Yap, Fallis Synthesis, p.921, 2000.

. Benzo, 1,3]dioxol-5-yl-pent-4-ynyl)-isoindole-1,3-dione

C. Nmr, CDCl 3 , 75 MHz): ?= 156.3 (C q ), 128.5 (CH), pp.70-77

1. Hz, 70 (br s, 1H), 4.15 (br s, 1H), 3.78 (s, 3H), 2. 47 (s, 3H), pp.0-9

D. E. Voir and . Lewis-angew, 6452 et les références citées. 12) a) K. Soai, S, 833 b) L. Pu, p.757, 1992.

A. O. King, E. Negishi, F. J. Villani-jr, and A. Silveira-jr, A general synthesis of terminal and internal arylalkynes by the palladium-catalyzed reaction of alkynylzinc reagents with aryl halides, The Journal of Organic Chemistry, vol.43, issue.2, p.358, 1978.
DOI : 10.1021/jo00396a046

L. Zhu, R. M. Wehmeyer, and R. D. Rieke, The direct formation of functionalized alkyl(aryl)zinc halides by oxidative addition of highly reactive zinc with organic halides and their reactions with acid chlorides, .alpha.,.beta.-unsaturated ketones, and allylic, aryl, and vinyl halides, The Journal of Organic Chemistry, vol.56, issue.4, p.1445, 1991.
DOI : 10.1021/jo00004a021

A. Krasovskiy, V. Malakhov, A. Gavryushin, and P. , Efficient Synthesis of Functionalized Organozinc Compounds by the Direct Insertion of Zinc into Organic Iodides and Bromides, Angewandte Chemie International Edition, vol.43, issue.36, p.6040, 2006.
DOI : 10.1002/anie.200601450

M. Amatore and C. Gosmini, Direct Method for Carbon-Carbon Bond Formation: The Functional Group Tolerant Cobalt-Catalyzed Alkylation of Aryl Halides, Chemistry - A European Journal, vol.78, issue.20, p.5848, 2010.
DOI : 10.1002/chem.201000178

URL : https://hal.archives-ouvertes.fr/hal-00506743

M. Amatore, C. Gosmini, and J. Périchon, (Bpy):?? An Efficient Catalyst for the Direct Conjugate Addition of Aryl Halides or Triflates onto Activated Olefins, The Journal of Organic Chemistry, vol.71, issue.16, p.6130, 2006.
DOI : 10.1021/jo060855f

L. Polleux-;-e, . Labbé-;-o, and . Buriez, CoI- and Co0-Bipyridine Complexes Obtained by Reduction of CoBr2bpy: Electrochemical Behaviour and Investigation of Their Reactions with Aromatic Halides and Vinylic Acetates, Chemistry - A European Journal, vol.562, issue.16, p.4678, 2005.
DOI : 10.1002/chem.200400971

K. B. Bahnk and S. D. Rychnovsky, Formal Synthesis of (???)-Kendomycin Featuring a Prins-Cyclization To Construct the Macrocycle, Journal of the American Chemical Society, vol.130, issue.39, p.13177, 2008.
DOI : 10.1021/ja805187p

E. Negishi, Palladium- or nickel-catalyzed cross coupling. A new selective method for carbon-carbon bond formation, Accounts of Chemical Research, vol.15, issue.11, p.340, 1982.
DOI : 10.1021/ar00083a001

A. O. King, N. Okukado, and E. Negishi, A general synthesis of terminal and internal arylalkynes by the palladium-catalyzed reaction of alkynylzinc reagents with aryl halides, The Journal of Organic Chemistry, vol.43, issue.2, p.358, 1978.
DOI : 10.1021/jo00396a046

E. Negishi, A. O. King, and N. , Selective carbon-carbon bond formation via transition metal catalysis. 3. A highly selective synthesis of unsymmetrical biaryls and diarylmethanes by the nickel- or palladium-catalyzed reaction of aryl- and benzylzinc derivatives with aryl halides, The Journal of Organic Chemistry, vol.42, issue.10, p.1821, 1977.
DOI : 10.1021/jo00430a041

N. Yoneda, S. Matsuoka, N. Miyaura, T. Fukuhara, A. Suzuki et al., Preparation of 1-Aryl- or 1-Alkenyl-2-(perfluoroalkyl)acetylenes, Bulletin of the Chemical Society of Japan, vol.63, issue.7, p.2124, 1990.
DOI : 10.1246/bcsj.63.2124

A. J. Lennox, G. C. Lloyd, and -. , Organotrifluoroborate Hydrolysis: Boronic Acid Release Mechanism and an Acid???Base Paradox in Cross-Coupling, Journal of the American Chemical Society, vol.134, issue.17, p.7431, 2012.
DOI : 10.1021/ja300236k

D. E. Rudisill and J. K. Stille, Palladium-catalyzed synthesis of 2-substituted indoles, The Journal of Organic Chemistry, vol.54, issue.25, p.5856, 1989.
DOI : 10.1021/jo00286a014

C. Lo-sterzo and J. K. , Use of palladium-catalyzed coupling reactions in the synthesis of heterobimetallic complexes. Preparation of bis(cyclopentadienyl)acetylene heterodinuclear complexes, Organometallics, vol.9, issue.3, p.687, 1990.
DOI : 10.1021/om00117a025

Y. Koseki and T. , Synthesis of Lennoxamine via the INtramolecular Cyclization of Alkynylamide., CHEMICAL & PHARMACEUTICAL BULLETIN, vol.43, issue.9, p.1604, 1995.
DOI : 10.1248/cpb.43.1604

Y. Koseki, K. Omino, S. Anzai, and T. Nagasaka, Silver salt-promoted direct cross-coupling reactions of alkynylsilanes with aryl iodides: synthesis of aryl-substituted alkynylamides, Tetrahedron Letters, vol.41, issue.14, p.2377, 2000.
DOI : 10.1016/S0040-4039(00)00167-2

J. Gil-molto and C. , Direct Coupling Reactions of Alkynylsilanes Catalyzed by Palladium(II) Chloride and a Di(2-pyridyl)methylamine-Derived Palladium(II) Chloride Complex in Water and in NMP, Advanced Synthesis & Catalysis, vol.348, issue.14, p.1874, 2006.
DOI : 10.1002/adsc.200606033

S. Chang, S. H. Yang, and P. H. Lee, Pd-catalyzed cross-coupling of alkynylsilanols with iodobenzenes, Tetrahedron Letters, vol.42, issue.29, p.4833, 2001.
DOI : 10.1016/S0040-4039(01)00811-5

S. E. Denmark and S. A. Tymonko, Cross-Coupling of Alkynylsilanols with Aryl Halides Promoted by Potassium Trimethylsilanolate, The Journal of Organic Chemistry, vol.68, issue.23, p.9151, 2003.
DOI : 10.1021/jo0351771

). R. Chinchilla and C. , Recent advances in Sonogashira reactions, Chemical Society Reviews, vol.74, issue.314, p.5084, 2011.
DOI : 10.1039/c1cs15071e

S. D. Roughley and A. M. Jordan, The Medicinal Chemist???s Toolbox: An Analysis of Reactions Used in the Pursuit of Drug Candidates, Journal of Medicinal Chemistry, vol.54, issue.10, p.3451, 2011.
DOI : 10.1021/jm200187y

A. Köllhofer and H. , A Convenient High Activity Catalyst for the Sonogashira Coupling of Aryl Bromides, Advanced Synthesis & Catalysis, vol.44, issue.9, p.1295, 2005.
DOI : 10.1002/adsc.200505095

A. Köllhofer, T. Pullman, and H. , A Versatile Catalyst for the Sonogashira Coupling of Aryl Chlorides, Angewandte Chemie International Edition, vol.42, issue.9, p.1056, 2003.
DOI : 10.1002/anie.200390273

M. Feuerstein, F. Berthiol, H. Doucet, and M. Santelli, Palladium-tetraphosphine complex: an efficient catalyst for the coupling of aryl halides with alkynes, Organic & Biomolecular Chemistry, vol.1, issue.13, p.2235, 2003.
DOI : 10.1039/b306428j

H. A. Dieck and F. R. Heck, Palladium catalyzed synthesis of aryl, heterocyclic and vinylic acetylene derivatives, Journal of Organometallic Chemistry, vol.93, issue.2, p.259, 1975.
DOI : 10.1016/S0022-328X(00)94049-X

L. Cassar, Synthesis of aryl- and vinyl-substituted acetylene derivatives by the use of nickel and palladium complexes, Journal of Organometallic Chemistry, vol.93, issue.2, p.253, 1975.
DOI : 10.1016/S0022-328X(00)94048-8

C. Yi and R. Hua, -Catalyzed Sonogashira Coupling of Aryl Chlorides with Terminal Alkynes, The Journal of Organic Chemistry, vol.71, issue.6, p.2535, 2006.
DOI : 10.1021/jo0525175

URL : https://hal.archives-ouvertes.fr/in2p3-00025581

D. Gelman and S. L. , Efficient Palladium-Catalyzed Coupling of Aryl Chlorides and Tosylates with Terminal Alkynes: Use of a Copper Cocatalyst Inhibits the Reaction, Angewandte Chemie International Edition, vol.42, issue.48, p.5993, 2003.
DOI : 10.1002/anie.200353015

D. C. Mcguinness and K. , Donor-Functionalized Heterocyclic Carbene Complexes of Palladium(II):?? Efficient Catalysts for C???C Coupling Reactions, Organometallics, vol.19, issue.5, p.741, 2000.
DOI : 10.1021/om990776c

Y. Ma, C. Song, W. Jiang, Q. Wu, Y. Wang et al., Sonogashira Coupling Using Bulky Palladium-Phenanthryl Imidazolium Carbene Catalysis, Organic Letters, vol.5, issue.18, p.3317, 2003.
DOI : 10.1021/ol035147k

C. S. Consorti, F. R. Flores, and F. Rominger, A Simple and Efficient Copper-Free Catalytic System Based on a Palladacycle for the Arylation of Alkynes, Advanced Synthesis & Catalysis, vol.208, issue.1-2, p.133, 2006.
DOI : 10.1002/adsc.200505310

K. W. Anderson and S. L. , General Catalysts for the Suzuki-Miyaura and Sonogashira Coupling Reactions of Aryl Chlorides and for the Coupling of Challenging Substrate Combinations in Water, Angewandte Chemie International Edition, vol.59, issue.38, p.6173, 2005.
DOI : 10.1002/anie.200502017

J. Li, Y. Liang, and Y. Xie, Efficient Palladium-Catalyzed Homocoupling Reaction and Sonogashira Cross-Coupling Reaction of Terminal Alkynes under Aerobic Conditions, The Journal of Organic Chemistry, vol.70, issue.11, p.4393, 2005.
DOI : 10.1021/jo0503310

B. Liang, M. Dai, and J. Chen, in Water under Aerobic Conditions, The Journal of Organic Chemistry, vol.70, issue.1, p.391, 2005.
DOI : 10.1021/jo048599z

K. Okuro, M. Furuune, M. Enna, M. Miura, and M. Nomura, Synthesis of aryl- and vinylacetylene derivatives by copper-catalyzed reaction of aryl and vinyl iodides with terminal alkynes, The Journal of Organic Chemistry, vol.58, issue.17, p.4716, 1993.
DOI : 10.1021/jo00069a040

M. Carril, A. Correa, and C. , Iron-Catalyzed Sonogashira Reactions, Angewandte Chemie International Edition, vol.48, issue.26, p.4862, 2008.
DOI : 10.1002/anie.200801539

D. N. Sawant, P. J. Tambade, Y. S. Wagh, and B. M. Bhanage, FeCl3/PPh3-catalyzed Sonogashira coupling reaction of aryl iodides with terminal alkynes, Tetrahedron Letters, vol.51, issue.20, p.2758, 2010.
DOI : 10.1016/j.tetlet.2010.03.063

H. Huang, H. Jiang, K. Chen, and H. Liu, Efficient Iron/Copper Cocatalyzed Alkynylation of Aryl Iodides with Terminal Alkynes, The Journal of Organic Chemistry, vol.73, issue.22, p.9061, 2008.
DOI : 10.1021/jo801942h

S. Protti, M. Fagnoni, and A. A. Angew, Photo-Cross-Coupling Reaction of Electron-Rich Aryl Chlorides and Aryl Esters with Alkynes: A Metal-Free Alkynylation, Angewandte Chemie International Edition, vol.45, issue.35, p.5675, 2005.
DOI : 10.1002/anie.200501541

J. Tang, Y. Xie, Z. Wang, and J. Li, Guo Synthesis, p.541, 2011.

G. Cahiez and O. Gager, Copper-Catalyzed Cross-Coupling of Alkyl and Aryl Grignard Reagents with Alkynyl Halides, Angewandte Chemie International Edition, vol.77, issue.7, p.1278, 2010.
DOI : 10.1002/anie.200905816

URL : https://hal.archives-ouvertes.fr/hal-00705984

W. B. Flynn and . Ogilvie, Arylzincation des Alcynes 1) a) A, Chapitre Chem. Rev. Acc. Chem. Res, vol.3, issue.41, p.1474, 2007.

J. Normant and A. , Alexakis Synthesis, p.841, 1981.

E. Shirakawa, S. Masui, R. Narui, R. Watanabe, D. Ikeda et al., Iron-catalyzed aryl- and alkenyllithiation of alkynes and its application to benzosilole synthesis, Chemical Communications, vol.14, issue.34, p.9714, 2011.
DOI : 10.1039/c1cc11989c

P. Forgione, P. D. Wilson, and A. G. Fallis, Magnesium mediated carbometallation of propargyl alcohols: direct routes to furans and furanones, Tetrahedron Letters, vol.41, issue.1, p.17, 2000.
DOI : 10.1016/S0040-4039(99)01995-4

P. Forgione, P. D. Wilson, G. P. Yap, and A. G. , Fallis Synthesis, p.921, 2000.

R. Nishimae, H. Inoue, and K. Shinokubo, Manganese(II) Chloride-Catalyzed Alkylmagnesation of 2-Alkynylphenol, Chemistry Letters, vol.27, issue.8, p.785, 1998.
DOI : 10.1246/cl.1998.785

K. Murakami, H. Ohmiya, H. Yorimitsu, and K. , Nickel-catalyzed Carbometalation Reactions of [2-(1-Propynyl)phenyl]methanol with 1-Alkenylmagnesium Reagents, Chemistry Letters, vol.36, issue.8, p.1066, 2007.
DOI : 10.1246/cl.2007.1066

D. Zhang and J. M. Ready, Iron-Catalyzed Carbometalation of Propargylic and Homopropargylic Alcohols, Journal of the American Chemical Society, vol.128, issue.47, p.15050, 2006.
DOI : 10.1021/ja0647708

Y. Yamamoto, H. Yatagai, and K. Maruyama, Stereocontrolled cis addition of organocopper reagents RCu.cntdot.BR'3 to .alpha.,.beta.-acetylenic carbonyl compounds, The Journal of Organic Chemistry, vol.44, issue.10, p.1744, 1979.
DOI : 10.1021/jo01324a047

J. K. Crandall, P. Battioni, J. T. Wehlacz, and R. Bindra, Dialkylcuprate-induced cyclizations of .omega.-halo-1-phenyl-1-alkynes, Journal of the American Chemical Society, vol.97, issue.24, p.7171, 1975.
DOI : 10.1021/ja00857a040

A. Alexakis, A. Commerçon, C. Coulentianos, and J. F. Normant, Alkenyl copper reagents???18, Tetrahedron, vol.40, issue.4, p.715, 1984.
DOI : 10.1016/S0040-4020(01)91100-7

J. K. Crandall and F. , Cis reduction of acetylenes by organocopper reagents, The Journal of Organic Chemistry, vol.41, issue.26, p.4089, 1976.
DOI : 10.1021/jo00888a009

E. Nakamura, S. Aoki, K. Sekiya, H. Oshino, and I. Kuwajima, Carbon-carbon bond-forming reactions of zinc homoenolate of esters. A novel three-carbon nucleophile with general synthetic utility, Journal of the American Chemical Society, vol.109, issue.26, p.8056, 1987.
DOI : 10.1021/ja00260a018

). S. Achyuta-rao, T. Chou, I. Schipor, and P. , Preparation and Reactivity of Polyfunctional Zinc and Copper Organometallics Bearing Sulfur Functionalities, Tetrahedron, vol.48, issue.11, p.2025, 1992.
DOI : 10.1016/S0040-4020(01)88872-4

C. Chen, G. Kehr, R. Fröhlich, and G. Erker, Carbon???Carbon Bond Activation by 1,1-Carboboration of Internal Alkynes, Journal of the American Chemical Society, vol.132, issue.39, p.13594, 2010.
DOI : 10.1021/ja106365j

M. Suginome, A. Yamamoto, and M. Murakami, Palladium- and Nickel-Catalyzed Intramolecular Cyanoboration of Alkynes, Journal of the American Chemical Society, vol.125, issue.21, p.6358, 2003.
DOI : 10.1021/ja0349195

M. Suginome, A. Yamamoto, and M. M. Angew, Palladium-Catalyzed Addition of Cyanoboranes to Alkynes: Regio- and Stereoselective Synthesis of ?,?-Unsaturated ?-Boryl Nitriles, Angewandte Chemie International Edition, vol.122, issue.16, p.2380, 2005.
DOI : 10.1002/anie.200462961

M. Muginome, M. Shirakura, and A. Yamamoto, Nickel-Catalyzed Addition of Alkynylboranes to Alkynes, Journal of the American Chemical Society, vol.128, issue.45, p.14438, 2006.
DOI : 10.1021/ja064970j

E. Shirakawa, K. Yamasaki, H. Yoshida, and T. Hiyama, Nickel-Catalyzed Carbostannylation of Alkynes with Allyl-, Acyl-, and Alkynylstannanes:?? Stereoselective Synthesis of Trisubstituted Vinylstannanes, Journal of the American Chemical Society, vol.121, issue.43, p.10221, 1999.
DOI : 10.1021/ja992597s

E. Shirakawa, H. Yoshida, T. Kurahashi, Y. Nakao, and T. Hiyama, Carbostannylation of Alkynes Catalyzed by an Iminophosphine???Palladium Complex, Journal of the American Chemical Society, vol.120, issue.12, p.2975, 1998.
DOI : 10.1021/ja974206k

Y. Shi, S. M. Peterson, W. W. Haberaecker, I. , and S. A. Blum, Alkynes as Stille Reaction Pseudohalides:?? Gold- and Palladium-Cocatalyzed Synthesis of Tri- and Tetra-Substituted Olefins, Journal of the American Chemical Society, vol.130, issue.7, p.2168, 2008.
DOI : 10.1021/ja710648b

K. Miura, D. Itoh, T. Hondo, H. Saito, H. Ito et al., Allylstannylation of alkynes via a radical process: stereoselective synthesis of di- and tri-substituted vinylstannanes, Tetrahedron Letters, vol.37, issue.47, p.8539, 1996.
DOI : 10.1016/0040-4039(96)01986-7

T. Konno, T. Takehana, J. Chae, T. Ishihara, and H. Yamanaka, Highly Regio- and Stereoselective Carbostannylation Reaction of Fluorine-Containing Internal Acetylenes with Allylstannanes, The Journal of Organic Chemistry, vol.69, issue.6, p.2188, 2004.
DOI : 10.1021/jo030272v

J. J. Eisch and J. , The question of allylic rearrangement in the reactions of tribenzylaluminum, Journal of Organometallic Chemistry, vol.30, issue.2, p.167, 1971.
DOI : 10.1016/S0022-328X(00)90196-7

J. J. Eisch, R. Amtmann, and M. W. Foxton, Proposed ??-complex intermediates in the reactions of organoaluminum compounds with alkynes. The behavior of tert-butylphenylacetylene, Journal of Organometallic Chemistry, vol.16, issue.3, p.55, 1969.
DOI : 10.1016/S0022-328X(00)89752-1

J. J. Eisch and C. K. Hordis, Organometallic compounds of Group III. XVI. Polar and stereochemical effects in the addition of triphenylaluminum to para-substituted diphenylacetylenes, Journal of the American Chemical Society, vol.93, issue.12, p.2974, 1971.
DOI : 10.1021/ja00741a026

G. Zweifel, N. L. Poston, and C. C. Whitney, A stereoselective synthesis of conjugated dienes from alkynes via the hydroboration-iodination reaction, Journal of the American Chemical Society, vol.90, issue.22, p.6243, 1968.
DOI : 10.1021/ja01024a068

D. E. Van-horn and E. Negishi, Selective carbon-carbon bond formation via transition metal catalysts. 8. Controlled carbometalation. Reaction of acetylenes with organoalane-zirconocene dichloride complexes as a route to stereo- and regio-defined trisubstituted olefins, Journal of the American Chemical Society, vol.100, issue.7, p.2252, 1978.
DOI : 10.1021/ja00475a058

D. E. Van-horn, L. F. Valente, M. J. Idacavage, and E. Negishi, Controlled carbometallation, Journal of Organometallic Chemistry, vol.156, issue.1, p.20, 1978.
DOI : 10.1016/S0022-328X(00)84891-3

E. Negishi, D. Y. Kondakov, D. Choueiry, K. Kasai, and T. Takahashi, Multiple Mechanistic Pathways for Zirconium-Catalyzed Carboalumination of Alkynes. Requirements for Cyclic Carbometalation Processes Involving C???H Activation, Journal of the American Chemical Society, vol.118, issue.40, p.9577, 1996.
DOI : 10.1021/ja9538039

S. Yamanoi, K. Seki, T. Matsumoto, and K. Suzuki, Regioselective alkylzirconation of internal alkynes, Journal of Organometallic Chemistry, vol.624, issue.1-2, p.143, 2001.
DOI : 10.1016/S0022-328X(00)00912-8

N. Suzuki, D. Y. Kondakov, M. Kageyama, M. Kotora, R. Hara et al., Novel type of carbozirconation reaction of alkynes, Tetrahedron, vol.51, issue.15, p.4519, 1995.
DOI : 10.1016/0040-4020(94)01138-P

T. Takahashi, D. Y. Kondakov, Z. Xi, and N. Suzuki, A Vinylzirconation Reaction of Alkynes, Journal of the American Chemical Society, vol.117, issue.21, p.5871, 1995.
DOI : 10.1021/ja00126a035

T. Takahashi, C. Xi, Y. Ura, and K. , and Chloroformate, Journal of the American Chemical Society, vol.122, issue.13, p.3228, 2000.
DOI : 10.1021/ja994234y

Y. Liu, Z. Zhong, K. Nakajima, and T. Takahashi, Alkynylzirconation of Alkynes and Application to One-Pot Bisalkynylation of Alkynes, The Journal of Organic Chemistry, vol.67, issue.21, p.7451, 2002.
DOI : 10.1021/jo026037e

B. Tan, J. Dong, and N. Yoshikai, Cobalt-Catalyzed Addition of Arylzinc Reagents to Alkynes to Form ortho-Alkenylarylzinc Species through 1,4-Cobalt Migration, Angewandte Chemie International Edition, vol.132, issue.38, p.9610, 2012.
DOI : 10.1002/anie.201204388

K. Murakami, H. Yorimitsu, and K. , Cobalt-Catalyzed Benzylzincation of Alkynes, Chemistry - A European Journal, vol.10, issue.26, p.7688, 2010.
DOI : 10.1002/chem.201001061

Y. Minko, M. Pasco, H. Chechik, and I. , 526 b) A. Basheer, I, Marek Beilstein J. Org. Chem. Marek Beilstein J. Org. Chem, vol.2013, issue.6 77, 2010.

M. Bakherad, A. Keivanloo, B. Bahramian, S. Jajarmi-applied-catal, J. R. Harjani et al., A: General 2010, 390, 135, p.650, 2010.

S. Urgaonkar and J. G. Verkade, Ligand-, Copper-, and Amine-Free Sonogashira Reaction of Aryl Iodides and Bromides with Terminal Alkynes, The Journal of Organic Chemistry, vol.69, issue.17, p.5752, 2004.
DOI : 10.1021/jo049325e