Selective oxymetalation of terminal alkynes <i>via</i> 6-<i>endo</i> cyclization: mechanistic investigation and application to the efficient synthesis of 4-substituted isocoumarins.
Kita, Yuji; Yata, Tetsuji; Nishimoto, Yoshihiro; Chiba, Kouji; Yasuda, Makoto; Chemical science 9 (2018) 6041–6052; doi:10.1039/c8sc01537f

data_1549560
_publ_section_title
;
 Selective oxymetalation of terminal alkynes <i>via</i> 6-<i>endo</i>
 cyclization: mechanistic investigation and application to the efficient
 synthesis of 4-substituted isocoumarins.
;
_journal_issue                   28
_journal_name_full               'Chemical science'
_journal_page_first              6041
_journal_page_last               6052
_journal_paper_doi               10.1039/c8sc01537f
_journal_volume                  9
_journal_year                    2018
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C16 H9 Cl O3'
_chemical_formula_sum            'C16 H9 Cl O3'
_chemical_formula_weight         284.70
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2017-09-25 deposited with the CCDC.
2018-06-14 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   3.8763(5)
_cell_length_b                   12.0424(19)
_cell_length_c                   26.146(4)
_cell_measurement_reflns_used    4965
_cell_measurement_temperature    123
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.12
_cell_volume                     1220.5(3)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_structure_refinement  'CRYSTALS (Carruthers, et al., 1999)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.952
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0776
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            10937
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.117
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.316
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_T_min  0.319
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             584.00
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.749
_refine_diff_density_min         -0.704
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1046 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.53(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2385
_refine_ls_R_factor_gt           0.0661
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
    Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979)
    3956.2700    5496.4800    1674.7600
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1165
_reflns_number_gt                2078
_reflns_number_total             2649
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c8sc01537f2.cif
_cod_data_source_block           1976
_cod_depositor_comments
'Adding full bibliography for 1549558--1549561.cif.'
_cod_database_code               1549560