Construction of C(aryl)-C(alkynyl) Bond from Copper-Mediated Arene-Alkyne and Aryl Iodide-Alkyne Cross-Coupling Reactions: A Common Aryl-Cu(III) Intermediate in Arene C-H Activation and Castro-Stephens Reaction.
Wang, Zu-Li; Zhao, Liang; Wang, Mei-Xiang; Organic letters 14 (2012) 1472–1475; doi:10.1021/ol300205r

data_1507169
_publ_section_title
;
 Construction of C(aryl)-C(alkynyl) Bond from Copper-Mediated Arene-Alkyne
 and Aryl Iodide-Alkyne Cross-Coupling Reactions: A Common Aryl-Cu(III)
 Intermediate in Arene C-H Activation and Castro-Stephens Reaction.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1472
_journal_page_last               1475
_journal_paper_doi               10.1021/ol300205r
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C30 H33 N7 Si'
_chemical_formula_sum            'C30 H33 N7 Si'
_chemical_formula_weight         519.72
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                79.649(10)
_cell_angle_beta                 71.640(10)
_cell_angle_gamma                76.483(9)
_cell_formula_units_Z            2
_cell_length_a                   10.2829(17)
_cell_length_b                   10.390(2)
_cell_length_c                   14.484(2)
_cell_measurement_reflns_used    4874
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      2.03
_cell_volume                     1418.5(4)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material  'SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_sigmaI/netI    0.0513
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12795
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.9875
_exptl_absorpt_correction_T_min  0.9686
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     350
_refine_ls_number_reflns         6377
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0714
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0495P)^2^+0.9993P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1512
_refine_ls_wR_factor_ref         0.1592
_reflns_number_gt                5442
_reflns_number_total             6377
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol300205r_si_002.cif
_cod_data_source_block           mx960
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1507169