Synthesis of 2-Alkenyl- and 2-Alkynyl-benzo[b]phospholes by Using Palladium-Catalyzed Cross-Coupling Reactions.
Matano, Yoshihiro; Hayashi, Yukiko; Suda, Kayo; Kimura, Yoshifumi; Imahori, Hiroshi; Organic letters 15 (2013) 4458–4461; doi:10.1021/ol401994e

data_1512303
_publ_section_title
;
 Synthesis of 2-Alkenyl- and 2-Alkynyl-benzo[b]phospholes by Using
 Palladium-Catalyzed Cross-Coupling Reactions.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4458
_journal_page_last               4461
_journal_paper_doi               10.1021/ol401994e
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C22 H16 Cl O P'
_chemical_formula_sum            'C22 H16 Cl O P'
_chemical_formula_weight         362.77
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.457(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.3504(2)
_cell_length_b                   7.9511(3)
_cell_length_c                   35.8818(12)
_cell_measurement_reflns_used    5503
_cell_measurement_temperature    143(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      3.08
_cell_volume                     1806.29(11)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_molecular_graphics    'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      143(2)
_diffrn_detector_area_resol_mean 14.629
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku Saturn70'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_sigmaI/netI    0.0279
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            14141
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.08
_exptl_absorpt_coefficient_mu    0.306
_exptl_absorpt_correction_T_max  0.9700
_exptl_absorpt_correction_T_min  0.8873
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4142
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0381
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0450P)^2^+0.8000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.0978
_reflns_number_gt                3841
_reflns_number_total             4142
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol401994e_si_001.cif
_cod_data_source_block           shelxl_2c
_cod_database_code               1512303